Dokumen.tips Bansal Classes Organic Chemistry Study Material for Iit Jee 1

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ORGANIC CHEMISTRY
XII (ALL)
QUESTION BANK ON
ACIDITY, BASICITY
H-BONDING
&
TA UTOMERISM
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ACIDITY. BASICITY. H-BONDING & TAUTOMERISM
Q. 1 Write equations showing the Lewis acid-base reaction that takes place when
(a) Methyl alcohol reacts with BF3.
(b) Methyl chloride reacts with AICI3.
(c) Dimethyl ether reacts with BF3.
Which ofthe following are lewis acids & which are lewis bases?
CH3
(a) CH 3 CH 2 -N-CH : (b) CH 3 -C® (C)(C6H5)3P:
CH3 CH3
( d) :Brf *(e) (CH3)3B (f) m
^/C?. 3 Which would you expect to be the stronger acid? Explain your reasoning in each instance.
' CH2C1C02H or CHC^CO.H
,Jb)
Jt) CC1
C
3C02H or CHC12C02H
H2FC0 2H or CH2FCH2C02H
Q. 4 Write equations for the acid base reaction that would occur when each of the following compounds or
solution are mixed. In each case label the stronger acid & stronger base,& the weaker acid & weaker
base.
(a) NaH is added to CH3OH
(b) NaNH2is added to CH3CH2OH
(c) Gaseous NH3 is added to ethyl lithium in hexane
(d) NH4C1 is added to NaNH2 in liq. NH3
(e) (CH3)3CONa is added to H 2 0
(f)
(g) NaOH is is
C2H5OH added toto
added (CH 3)3 C-OH
a solution of HC = C~Na+ in liquid NHV
Q.5 CHjCHjMgBr + CH3C = CH >A +B
Choose the member of each of the following pairs of compunds that is likely to be the stronger base.
v (a) NH 2 or NH3 ( Jb) OH orH 2 0 J c ) O H or SH
o- O
©
4
Choose the member of each of the following pairs of compunds that is likely to be the weaker base.
2
H 2 0 or H30® v , (b) H2S, HS- S ~ (C) CI", SH
Jd^F-, OH~ MTV, CH3 J e ) HF, H 2 0, NH3 , OH- SH", SeH
<j| Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [2]
Q.8 Label the reactants in these acid - base reactions as Lewis acids (electrophiles) or Lewis bases
(nucleophiles). Use curved arrows to show the movement of electron pairs in the recations.
(A) CH 3 O : +C H 3 -CI: - > C H , -• O

• ^ C H V + l•C• i r
(b) CH3-O-CH3 + :O- H—> CH 3 -O: +C H^ -P -H
CH 3 H CH 3 H
O :o:
(c)
II
H - C - H + :NH 3 ->H-C=RH
2
IS M
NH 3
(d) CH 3 - N H 2 + CH 3 - CH 2 - CI: —- > CH3 - N H 2 - CH 2 CH 3 + :CI:
(e) (CH 3)3CC1 + A1C13 > (CH 3)3<?HÂ1C14

JL4
(f) + BR B E> — CH-J — C HO
M
"Or
CII3 -FC»*CHFÔ - H CH3 - c = CH 2 +H - O - H
(h) BF3 - C H 2 -C H 2 + C H ^ C H , B F3 — CH 2 — CH 2 — CH 2 — C H 2
CH3 - c - CH3 + H 2SO4

R
© CH 3 - C - CH 3 + HSO4
f A
Q. 9 Predict the products of the following ac id ba se reactions.
H 2 S 0 4 + CH3COO- ^
Q.10 Methyllithium (CH 3Li) is often used as a base in organic reactions.

(a) Predict the produc ts of the following acid - base reaction.
CH 3CH2 - O H + CH3 - Li >
(b) What is the conjugate acid of CH3Li ? Would you expect CH3Li to be a strong base or a weak base ?
Q.ll Which reagent in each pair listed here would be the more reactive Nu in a protic solvent ?
xJ$) CH 3 NH- or CH3NH2 (b) H 2 0 or H,0®
y M CH 3 0- or CH 3 COO ^ (d) CH 3 SH or CH 3 OH
k) Ph3 N or Ph 3 P CH 3 COO" or OH
H.S orHS" NH 3 or NH4®
Q.12 Each ofthese molecules is electrophile. Identify the electrophilic atom & draw a mechanism for reaction
with a generalised nucleophile Nu", giving the product in each case.
F° V Y X
(a) (b) Y (c) [ J (d) CI - CI (e) MeO ® OMe
19 Explain whic h comp ound is the wea ker base.

NH 2 N H2
rol^Ta
^ b f . CH 2 = C H - C H = C H -C H 2" or CH^CH-CIV
0 0 0 0
II II II II
J t f 0--C-C-0H or HO -C- C- OH
OH OH
1
j * ( o r * - [ o r "
Q. 20 Rank the following amines in increasing basic nature.

NH.
•NO,
« [OJ [or LO
(i) (ii) * (iii) (iv)
NHt
NH2
1
0» f o r " L Q „„
CH 3
(i) (ii) (iii) (iv)

NH 2
(c> ©
(i) (ii) (iii)
Q. 21 Dimethyl furmam ide (DM F) is an example of polar aprotic solvent, aprotic meaning it has no hy drogen
atoms attached t o highly electronegative atoms.
(a) Dra w what you predict to be its mos t import ant reson ance forms.
(b) DM F whe n used as the reac tion solvent, greatly enhances the reactivity of nucleophiles. e.g.
Na CN + CH 3 CH 2 Br > CH^ CIi , C = N + NaB r
Suggest an explanation for this effects.
Q. 22 Arrange the basic strength of the following compounds,

(a) OH- CH3COO- Gi-
ft (ii) (iii)
Or) CHeC" CH 2 = CH- C H 3 C IV
(i) (H) (iii)
(pf CH2 = CH CR j NR , CT^CI^CI^ML, CH = C - C i ^ W ^
^ 0) Oi) d)
<|g Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [5]
Q.13 Each ofthese molecules is nucleophile. Identify the nucleophilic atom & draw a mechanism for reaction
+
with a generalised electrophile E , giving the product in each case.
W R- C. C- w J X (ONH.-NH,
OMe
I NH
p IT
( d ) M e O / ÔMe (e) M ^ M e
^,-Q. 14 Arrange the following compounds in order of increasing basicity.

^ CH3NH2, CH3 NH®, CH3NH
x&f " CH3 0- CH3NH-, CH 3CH 2
yjdf CH3CH = CH", CH3CH2 CH2 , CH3C=C
Q.15 Neither of these methods of making pentan-1,4 diol will work. Explain why no t- wh at will happen
instead?
MeM
(i) CH0-CH 2 -C H 2 -C H 2 -0H - ^ > CH3- CH- CH2 -CH2 - CH2
+
followed by H | |
OH OH
(ii) Br-CH 2-CH 2-CH 2-OH MgBr-CT^-CH^CHÔH f
C H 3 - C H - C H 2 - C H 2 -C H 2
I I
OH OH
Q 16 Suggest what species would be formed by each of the following combinations:
(a) PhO - + CH3COOH
( b ) H N ^ N H + CH 3 COO-
(c) Pyridinium ion+trifluoroacetate ion
Q.17 Say which pka belong to which functional group in case of following amino acids:
^COOH
(i) cysteine: HS J : 1.8,8.3 & 10.8
NH2
(ii) glutamic acid : H 0 2 C \ ^ \ ^ C O O H . 2 ]9> 4 25, 9.67

NH2
Q.18 Record the following sets of compounds according to increasing pKa ( = - log Ka)
OH OH
(a) C ^ J ' (Ô J ' cy cl°hexane carboxylic acid.
^b) 1-butyne, 1-butene, butane

Propanoic acid, 3-bromopropanoic acid, 2-nitropropanoic acid
)JfSf Phenol, o-nitrophenol, o-cresol
Hexylamine, aniline, methylamine
<f| Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [5'5]
NH2 NH-C 6 H 5 NH2
^ LO
(i) (ii) (iii)
NH ,
NH,
VÔ fO
o CI
(iii)
(i) (ii)
ci - RCOO- 0H- RO - NH 2 -
(i) (ii) (iii) (iv) (v)
Q.2 3 Set the followin g in increasing orde r of pk b :
ff
^NH
© § NH
J® CH 3NH2 , ( CH 3 ) 2 N H, (CH3 ) 3 N, NH 3 [In aqeous medium ]

NH
-NH2
h' (iii)
J*
Q.24 Arrange the following in increasing acid s treng th:
o
_ T-C-CH,
(a) =o O f o
OH
(i) (iii)
OH
OH
O, CH 3 - OH
CN
(i) (ii) (iii)
O O O 0 O
C H3 -C-OH H 0- C -C - 0H H O- C- CH 2 C H 2 J- OH
©
(ii) (iii)
v yO .25 Set the following in increasing order of pk a:
jffi Methane sulfonic acid, acetic acid & methanol.
{ CH 3 - CH2 - CH 3 , CH2 = CH - CH3 , CH3 - CHO , CHO - C H j - CHO , CH4 Ui) ^
^Jfy C H 3 N 0 2 , ( N 0 2 ) 2 - C H 2 , ( N 0 2 ) 3 -CH
n uH 9H
OH 9 OH X.
^ ho2 N °2 -
^Jy) CH3COOH, N 0 2 - C ^ - COOH, CH3 - C - CH 2 - C - OH
o o
. . CN CN
^ Q-Q-J&
H H H H H CN
^ fafff CH O-C HL- CHO , C H 3 - C

II - C H 2 - C0
0 II- C H 3 , E t - 0 - C0
II - C H 2 - C0
II-•O - E t ,
Et - O - C - CH 2 - C - CH 3
II II
0 0
Q. 26 Cyanic acid (HO-CsN) & isocyanic acid (H-N=C=0) differ in the positions of their electrons but their
structure do not represent resonance structures.
(a) Explain
(b) Loss of a proton from cyanic acid yields the same anion as that obtained by loss of a proton from
isocyanic acid. Explain.
i
Q. 27 Draw a mechanism for this reaction.

PhCHBrCHBrC0 2H + NaHC0 3 > PhCH=CH-Br + C0 2
Q.28 Arrange the increasing order of acidic strength ofthe following compounds.
v>r ^ rb Col™,
CH,
(i) (ii) (iii)

CH 2 C0 2 H
(b) [QJ CH 2 =CH-CH2 C0 2 H CH ^ CO . H
(i) (») <*)

CH3OH CF3OH CCI3-OH
(i) (ii) (iii)
[7]
<j| Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism
x-(¥29 Explain which is a stronger acid.

O O
^ a ) CH3CH3 BrCt^NO,, CH3 - C - CH3 & CH3 - C - CH2CN

OH .
^ C O ) or J d ) ( 0
O=C~CH3 ' O=C-CH3 CH3
SH OH
Mo) <* ( O )
^jaf.5 0 Which ofthe following would you predict to be the stronger acid ?
^Jb) CH3 - CH2 - CH2 - OH or GH3 - CH = CH - OH

^Jc) CH3 - CH = CH - CHj - OH or CH3 - CH = CH - OH
Which is a stronger base? & Why.

ethylamine or aniline (b) ethylamine or ethoxide ion
yj^p henoxide ion or ethoxide ion \J<€) cyclohexylamine or aniline
TheKaofphenylaceticacidis 5.2 x 10~5, and the pKa of propionic acid is 4.87.
y~CH 2-C-QH C H 3 -C H 2 -C-OH
phenyiacetic acid,5 propionic acid,

Ka = 5.2 x 1(T pKa = 4.87
J(s) Calculate the pKa of phenyiacetic acid and the Ka ofpropionic acid.
Jfo) Which of these is the stronger acid?
Jjz) Predict whether the following equilibrium will favor the reactants or the products.
< Q - C H 2 C O O ° +CH3CH2COOH <^y~CH 2 C O O H + CH3CH2COO®
Q. 3 3 Explain why the 2-methylpyrrolidine boils at a higher temperature than its isomers N- methylpyrrolidine.
U- UneO'l
Q. 3 4 Although nitration usually causes elevation of B .P. yet the nitration of resorcinol to 2-nitroresorcinol
decreases their B. P. then their parent compound.
5 o-nitrophenol is sparingly soluble in water & has lower B .P. but p-nitrophenol is completely soluble in
water & has high boiling point.
r
6 When 3 0 ml of ethanol and 5 ml of water are mixed the volume of the resulting solution is less than
35 ml. Explain.
^ Ammonium salts are much more soluble in water than are the corresponding sodium salts. Explain?
QS 8 HF has a dipole moment of 1.82 D, its boiling point is 19.34°C. Ethyl fluoride has an almost identical
diploe moment & has a larger molecular weight, yet its B.P. is -31.TC. Explain.
J&39 HC02H & CH3C02H exists as dimer. Explain.
Q. 40 Cyclohexanol is more soluble in water then 1 -hexanol.
Q. 41 Explain why CH3OH and CH3CIÔH are reasonably good solvents for many ionic compounds compare
the solvent properties of ethanol and pentanol towards ionic compound.
Q.42 1,5-Pentanediol is soluble & 1-Pentanol is slightly soluble in IÔ .
\J#A3 Compare the relativî^ oiling points Water solubilities oftoluene & phenol.
Q.44 Which isomer (o,m or p) ofhydroxacetophenone steam distills.
J^45 Give structure for ethanolamine showing two different intramolecular H-bonds & discuss their relative
strength. f
Q.46 Which ofthe following system show H-bonding during tautomerism.

O N-H
(a) o
OK^ = M
v r v >o0 ..
(b) Q (c) A ( d ) ( \
W W
H
NC^H HoXr
HOaH
Q. 47 Trans isomer ofindigotin is stable w.r.t cis isomer. Explain.
A
Q. 4 8 What is the attacking site of conjugate base oftriketo form ofphloroglucinol in protic & aprotic solvent.
\JQC49 In each oftheôllowing pairs which is more stable:
H (I) (11)
O O
0 H
C / C /OH
(I) (nf C"3 (1) N "2 (J ^NH
0
0 H
C /
u (11)
In each of the following pairs which is less stable:
o o
C /OH £ /OH
(I) U)
(11) (ID
O
£ / 0 H
(I) (II)
0II 0
I!
O
U
OH
X
c c c c
e N
()a / V CH3 - cuf V ^CH2
3 3 3
a) ao
yjtf.51 In each ofthe following pairs which is more stable:
o o f crH o
c c c c
/ X N
caf
3
\H 22 CH3 CH^ CH3
(I) (II)
H O O L,
O^ a-0 0C__^0 fj CH, £ %
j » 0 ©
O (ii)
« ^ vo w CHy2
(1) (II)
CH,
g CH CH O7" °" f
CH
OH
(IT) ...
(1) O CH, (II)
d#52 In each ofthe following pairs which is less stable:

OH
1
,0 '
O
U
O^ O OH
(0 (II) ^H (I) (II)
Ph Ph Ph Ph
N = NH
\ ($fCH22 = CH - NH2 ^ CH3-CH
^0 ^ OH (1) ^ (II)
(I) (II)
Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [10]
Q. 53 In each ofthe following pairs which will have higher enol content:
O ^COOEt ft
C
i Jti) CHX HO and / \ (b) C \ and
X
^ CH 3 CH 3 C O O Et CH3 CH 3
^COOEt ft ft
(c) C \ and
COO Et CH CH OCH
3 2 3
. FL FF " FL ' FL
C c
v and / \ / \
^ CH 3 CH 2 CH 3 CH 3 CH 2 OCH 3
0 0 0 0
II II II II
(e) and
CH 3 CH 2 CH 3 Ph CH 2 Ph
Q. 54 In each ofthe following pairs which will have less enol content:
^ C ^ V V ( b ) C T ° a n d Q °
and
and Q ° ^ ( ^ f
J * ) C H 2 - CHO and CH 3 - CHO
CI
Q. 5 5 In each ofthe following pairs which will have higher enol content:
II O
11
c
CH 2 - C H O and CH 2 -C HO (b) ( qY \ r and y\
I I 3 CH 3 CH 3
NO 2 CI
(c) [OJ CHO and[OJ^ CHO

0 H
OH
o o
0 0 c r
A A j / \ / \
v > 0 / \ / \ and CH 3 CH CH 3
CH 3 CH 2 CH 3 ^2H5
(§ Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [11]
In each of the following pairs which will have less enol content:
\ /OCH3 V / O C H :
(a)
0 ^ 0 ® -"Sr
O ^ C P andCP J d ) h > = 0 and h > 0

0 0
r.
TjJ^ 0
and ^ ^ o
H H
57 Which ofthe following compounds can exhibit tautoimerism:
(a) CHj = C = O (b)CH2 = C H - 0 H (c) HO- CH = CH -O H
(d) CH3CN (e) C \

^NO2
8 Which ofthe following compounds can not exhibit tautoimerism:
0 O II
o
0
(d)(6r ^ (e)@r°H
Which ofdie following compounds can exhibit tautoimerism:
0
NH
Which ofthe following compounds can not exhibit tautoimerism:
f r
« y ^
OMe
(d) Ol I OJ (e) CH3 - NO

61 what is the relationship between these two molecules? Discuss the structure of the anion that would be
formed by the deprotonation of each compound.
11
->A JL
I N5" "OH
H
Q. 62 5,5 - dimethylcyclohexane -1,3 -dione (dimedone) shows tautomerism.Write down tautomeric structure.
Q. 63 Draw enol forms of these carbonyl compounds and comment on the stability of the enol forms.
(a) " a
o »>oo
o
Q. 64 The proportion of enol in a sample ofthe two ketones below are shown. Why are they so different ?
O O
4x % enol (b) ( ^ J ^
CH BO ^^ -X ^MI - CH = CH2
Q.65 (a) Jf J
and
CH = CH2
a
< » CU
Shows tautomeric forms of (a) & (b).
Q. 66 Isatin was thefirstcompound to show tautomerism.
ex?
"N : I
H
What is the tautomeric form of isatin.
Q. 67 available
1 , 3 - dicarbonyl compounds
to compounds A & B such as (A)
comment theusually
onare mostly
different enolized.
pattern Why is this ? Draw the enols
of enolization.
Q. 6 8 In each of the following sets of compounds write the increasing order of % enol content
JSC (0 <TI> 6 A(HI) (IV)
(gong;
N 0
(I) (11) 2
O2N
, —i § n m
— NO 2
(IIJ)
(C)
(grv ^ o
(LI)
(1) NO, (111)
NO 2
(II) (111)
NO,
CI
Ct
O I
o
u^LQj o
© (11) (III)
Q. 69 In each of the following sets of compounds write the decreasing order of % enol content.
O
(SQ
(a) 0 C O ail)
(I) (II)
0» o 0
(i) (II) (III) (IV)
o
j a)y cNr
(11) (III) (IV)
o o
(d) o ^ j y o N"
H
o.
H
(1) (ii) (HI) (IV)
o
o O
(e)
a) (HI) (TV)
(II)
( S | Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [14]
Q. 70 Enol form of cyclobutanone is very unstable vs enol form of triketocyclobutane, which is very stable.
Q.71 Â^Â^ has lower boiling point than even when former has - OH group.
O O
Q-72 C H { AN C H 3 C D 3 /AX C D 3 CH 3 a \ N 2
Y AX C H 3
(i) y do (in)
Among these give ease of enolization.
Q. 73 % enol content of acetylacetone in following solvents is found as:

Solvent % enol content
HjO 15
Liquid state 76
hexane 92
92
Explain the observation.
@ @ + ©©
Q.74 J k ^ ?
(Minor) (Major)
Na0Hl[,H20
O
OH , OH
(Major) (Minor)
Explain the observation.

O OH
This tautomeric system exist almost exclusively in favour of phenol and it is insensitive to change in
solvent.
ANSWER KEY
Q.2 LA b,e LB acdf
Q.3 (a) 2; (b) 1; (c) 1
Q. 5 C H3 C H3 + C H 3 C s C M g B r
Q.6 (a) 1; (b) 1; (c) 1; (d) 1; (e) 2; (f) 1
Q.7 (a) 2; (b) 1; (c) 1; (d) 1; (e) 1; (f) 3
Q. 11 (a) 1; (b) 1; (c) 1; (d) 1; (e) 2; (f) 2; (g) 2; (h) 1
Q.14 (a) 2<1< 3; (b) 1<2<3; (c) 3<1<2
Q.18 (a) 3<2<1; (b) 1<2<3; (c) 3<2<1; (d) 2<1<3; (e) 2< 3<1
Q.19 (a) 2; (b) 1; (c) 2; (d) 2
Q.20 (a) 3<2<1< 4; (b) 1<2<3<4; (c) 3<1<2
Q.22 (a) 1>2>3; (b) 1<2<3; (c) 3<1<2; (d) 2<1<3; (e) 1<2<3; (f) 1<2<3<4<5
Q.23 (i) 1>2; (ii) 4>3 >1> 2; (iii) 1<2; (iv) 1<2
Q.24 (a) 1<2<3; (b) 3>1>2; (c) 1<3<2
Q 25 (i) 1<2<3; (ii) 1>5> 2>3> 4; (iii) 1>2>3; (iv) 1>3>4> 2; (v) 1>3>2; (vi) 2>1> 3;
(vii) 3>4>2>1
Q.28 (a) 3>1>2; (b) 1>2>3; (c) 2>3> 1
Q.29 (a) 2; (b) 2; (c) 1; (d) 1; (e) 1
Q.30 (a) 2; (b) 2; (c) 2
Q.31 (a) 1; (b) 2; (c) 2; (d) 1
Q.32 4.25,1.34><10_5
Q.49 (a) 2; (b) 2; (c) 1; (d) 1; (e) ^
Q.50 (a)2; (b) 2; (c) 2; (d) 2; (e) 1
Q.51 (a) 2; (b) 2; (c) 1; (d) 2; (e) 1

Q.52 (a) 2; (b) 1; (c) 1; (d) 1
Q.53 (a) 1; (b )l ; (c) 2; (d )l ; (e) 2
Q.54 (a) 1; (b) 1; (c) 2; (d) 1; (e) 2
Q.55 (a) 1; (b) 1; (c) 1; (d) 1
Q.56 (a) 2; (b) 2; (c) 2; (d) 1; (e) 2
Q.57 a, b, c, d, e
Q.5 8 a, c, d
Q.59 b
Q.60 b
Q.68 (a) 2>1>4 >3; (b) 3>2>1; (c) 3>2>1; (d) 3>1>2; (e) 3> 1>2
Q.69 (a) 3>1>2; (b) 4>2> 1>3; (c) 4>3>1 >2; (d) 1>3>4>2; (e) 3>2>4 >1
Q.72 3>1>2
4g Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [16]
BANSALCLASSES
TARGET IITJEE 2007
ORGANIC CHEMISTRY
XII (ALL)
ALCOHOL & ETHER
CONTENTS
EXERCISE-1(A)
EXERCISE 1(B)
EXERCISE-II
EXERCISE-III
EXRECISE - IV(A)
EXRECISE - IV(B)
ANSWER KEY
EXER CISE-IfA)
Q. 1 Which of the following reaction is called as 'Bouveault-Blanc reduction'

(A) Reduction of acyl halide with HyPdBaSC^
(B) Reduction of ester with Na/CÔ H
(C) Reduction of anhydride with Li A1H4
(D) Reduction of carbonyl compounds with Na/HgHCl
Q.2 Glycol on treatment with PI3 mainly gives-

(A) Ethylene (B) Ethylene iodide (C) Ethyl iodide (D) Ethane
Q.3 Acrolein is formed when glycerol is heated w ith-

(A) Acidified KMn04 (B) Br2 water (C) KHS0 4 (D) HN0 3
Q. 4 Glycerol on treatment with oxalic acid at 110°C forms-

(A)Allyl alcohol (B) Formic acid (G) C0 2 and CO (D) Glyceric acid
Q. 5 If the starting material is 1-methyl-1,2-epoxy cyclopentane, of absolute configuration, decide which

one compound correctly represent the product ofits reaction with sodium methoxide in methanol.
Q. 6 When phenol is treated with PC15, the yield of chlorobenzene is generally poor because ofthe formation
of
(A) Benzoyl chloride (B) p-chorophenol (C) o-chlorophenol (D)Triphenyl phosphate
Q. 7 In the following reaction,finalproduct is

14
CICH2CH-CH.2 NaOC2H<
14 14
(A) CICH2CHCH2OC2H5 (B) ClCH2CHCH2ONa
OH
14 14
(C) CH2-CHCH2OC2H5 (D) CH2-CHCH2OC2H,
fe Bansal Classes Alcohols & Ethers [13]
Q. 8 Consider the reaction of HI with the following:
• 0 • § 0
Which forms di-iodide on reaction with HI (excess)?
(A) I and II both (B) II only (C) I only (D)none
Q. 9 Ethanol on reaction with acetic anhydride gives
(A) Acetic ester (B) Formic ester
(C) Ethanoic acid (D) Acetic ester and Ethanoic acid both
Q. 10 Ethanol cannot be dried by anhydrous CaCl, due to formation of the following solvated product
(A) CaCI2-2C2H5OH (B) 2CaCl2-3C,H5OH (C) C a C l ^ C ^ O H (D) CaCl2-C2H5OH
Q. ll Rate ofhydration of
will be in order:
(A) I < II < III (B) I < III < II (C) II < I < III (D) III < II < I
Q . 12 The reaction of CH3OC2H5 with HI gives
(A)CH3I ~ (B)C 2H5OH (C) CH3I + C2H5OH (D)C 2H 5I + CH3OH
Q.13 The number of methoxy groups in a compound can be determined by treating it with
(A) HI and AgNO, (B) Sodium carbonate (C) Sodium hydroxide (D) Acetic acid
Q. 14 Most acidic alcohol out of following compounds is
(A) (CH3)3C-OH (B)CH3CH2OH (C)CH3OH (D)PhOH
Q.15 Action of HN 0 2 on CH3NH2 gives following as major product
(A) CH3OH "(B) CH 3 -0-CH 3 (C) CH 3 -0-N=0 (D)CH 3 -N 0 2
Q . 16 A compound 'X' with molecular formula C3HgO can be oxidised to a compound' Y' with the molecular
formula C1H602, 'X' is most likely to be
(A) Primary alcohol (B) Secondary alcohol (C) Aldehyde (D) Ketone
Q.17 Diethyl ether and air gives ether hydroperoxide. The mechanism ofthe reaction is
(A) Nucleophilic substitution (B) Free radical addition
(C) Free radical substitution (D) None of the above
Q.18 Ether on carbonylation gives

(A) Alkanoic acid (B)Alkanone (C)Alkylalkanoate (D)Alkanal
Q. 19 I 0 R - O- R • > RI + R'OH true about this mechanism

i
H
(A) SN1 in gas phase (B) SN2 in aqueous phase
(C) both of the above (D) none
Q 20 Phenol with Hinsberg's reagent gives

(A) Sulphone (B) Sulphanilic acid (C) Sulphonic ester (D)Sulphonal
0 .21 Select the odd structure out

(A) CH3 -CH(OH)-CH 2 -CH 3 (B) CH r CH(OH)-CH 2 -CH,-CH 3
(C) CH3-CH(OH)-CH3 (D) CH 3 -CH 2 -CH(0H)-C2 H 5
„ „ , KHSO, * LiAlH4
Q.22 Glycerol A
A and B are :
(B) Glyceryl sulphate, acrylic acid
(A) Acrolein, ally! alcohol
(D) Only acrolein (B is not formed)
(C) Ally] alcohol, acrolein
Q 23 An ether is heated with phosphorous penta sulphide to give
(A)Alkanthiol (B) Dialkyl sulphide (C) Hydrogen sulphide (D)Thioester
H+/H2
Q.24 Phenol A ° >B ^ » C
(ii)C02/140°C CH3COOH,A
In this reaction, the end product C is:
(A) salicylaldehyde (B) salicylic acid (C) phenyl acetate (D) aspirin
Q.25 In the Liebermann's nitroso reaction changes in the colour ofphenol occurs as:
(A) Brown or red-greenish red-deep blue (B) red-deep blue-green
(C) red-green-white (D) white-red-green
Q.26 ^ A. 'A'is
CH2OH
CH2OH
(C)
•CH,
7 r > cH3 cold v

>A
CrO,
>B
Q. 27 I^ IJ alkaline K M N 0 4 " ACO H
A and Bare:
.CH, CH,
OH J ^ ^ O L L
(A)
OH'I J= 0
CH3 CH3
(C) OH OH (D) no formation ofA and B

OH '
fa Bansal Classes Alcohols & Ethers [36]
Q.28 B *
NaBH,
r v CH = CH - CHO H2/Pt
>A
A and Bare:
(A) ( V CH 2 CH 2 C H 0 , ( / - C H = CH-CHJOH
(B) ^ / - CH 2 CH 2 CH 2 OH, J - CH = CH - CH 2 OH
(C) ( JV - CH= CH-CH 2 OH in both cases

CH= <
(D) CH 2 C H 2 C H 2 0H in both cases
CH,
CH,OH h
Q.29 B 4r CH.-C-CH, 2° 18 >a
CH,ONa \J " H+
o
A and B are
CH, CH, CH, CH,

l
3 ~ 3
(A)CH,-C-C H, ,CH 3-C-CH2 (B) C H 3 - C — CH 2 , C H 3 - C - C H 2
OH OH OH OCH, OH l g OH OH OCH,
18
CH, CH, CH, CH,
(C) CH 3 - C - C H , , CH, - C — CH, (D) C H , - C — CH, , CH, - C — CH,
IBOH OH
18 18
0 OH OH 3 OH OH OC H 3 OH
Q.30 Oxalic acid + A >
henceA ^B ,B is :
0 = ^
(A) (B) (C)CH2-0-CH2 (D) None

OH OH
' CH2CH3 rH=PH_

K
0H
Q.31
CH2CH2OH
Select schemes A, B, C out of

I acid catalysed hydration II HBO !IS oxymercuration-demercuration
(A) I in all cases (B) I, II, III (C) II, III, I (D) III, 1, II
Q 32 Dehydration of the alcohols
-OH
-OH
OH OH
(I) (II) (III) (TV)
will be in order
(A) IV > III > II > I (B) I > II > III > IV (C) IV > II > III > I (D) II > IV > I > III
Mg/ether
Q 33 CI-LMgBr ^ A R > r. — H I F,
H,0+
E is
(A) (B) (Q (D)
CH3 CH2I CH2CH3 CH, CH,
OH OH
Et
Q.34 H+ ^ ? Product is:
•Me o Ox /Et
(A)
H CI Ale. KOH
Q 35 \ 0 / \ / \ / > Majo r product is
(A) H \ 0 / V ^ / U \ „ (B) H \ q A A
H
(C) \ / \ / \ (D)
0
CJ
x r
fa B a n s a l Classes Alcohols & Ethers [36]
o
RMgX
Q.36 ? Pro du ct Obtained is:
R' H2O
R"
R R' R R
(A)R'-C-CH2OH (B )R CH 2 -C-0H (C)R 'GH2-C-O H (D)R "CH 2 -C -O H
R" R" R" R'
0 OH
R H I, /NA OH , . . .
Q.37 CH, 2 ^ H+ ^ A ) A, A IS
o o
0 0 II
II
C-OH Cs
~OCH,
(A) <B>pr (C) (D)
Q.3 8 (A) < CH3

°H "*(B)A&B are:
H 2 SO 4
\H Of H OCH,
\H CP 3 \H ?P H 3
(A) & (B) yj( &
ch H3 CO CH3 HO CH 3
H.CO OH OH 3
(C) & CD)"

H OH MeO CH 3 H 3CO OH H 3 CO OH
Q.39 OCOCH3 AICI3 > 7 Maj or Produ ct is:
(B) H 3 CO C
OH
(°)\Or\Oy~
COCH,
<!§Bansal Classes Alcohols & Ethers m
O-CH 2CH=CH 2
A
Q.4 0 Y Q Y ^, ? Product is:
OH OH
/R R\/ /R
(A) (B)
CH2CH=CH2 CH 2 -CH-CH7
OH
R V A / R
(c) (D) no reaction

iJSi CH2—CH—CH9
OH
(i)CHCS3+KOH
Q.41 [X] here 'X' is:
OH (ii)CH 2 I 2 +NaOH
OH
(A)
HOOC' ^
j c g f OH X O H C
/
\ ^
N
O H
OCH3
(C) l O l / H : (D)
OHC OHC OCH3
/OH OH
Q.42 Inthisdiol
(A) OH at C2 is more basic than that of at C5 (B) OH at C2 is more acidic than at C5.
(C) both have same basicity (D) both have same acidic strength
0H
Q.43 (CH3)2C = C(CH3)2 — A ~ >B
H,O
(A) (CH3)2C-C(CH3 )2 (B) (CH 3 ) 2 C-C(CH 3 ) 2

I I
O OH CI
(C) (CH 3 ) 2 C-C(CH 3 ) 2 (D) None

I I
OH OH
OH CH 2 -NH,
NaNO,
Q.44 | | >A
HCl
A is
OH CH-,-OH OH CH2-C1 OH CH 2 -NO, Q
(A) (B) ( C ) f l ( D ) f S
i&Bansal Classes Alcohols & Ethers fSJ
Mn0
Q.45 CH 2 =CHCHCH 2 CH 2 OH - -- )A.Ais
OH
(A) CH 2 = CHCCH 2 CH 2 OH (B) CH 2 = CHCHCH 2 CHO
O OH
(C) CH. = CHCCH„CHO (D) CH 2 = CHCCH 2 COH

I!
o o
+
^ . HCO,H
2 . H,
20 „ , „ PthalicAnhydride
Q4b Acetophenone —> A >B + C ; > Indicator (D)
C & D are
X K /—OH
( A ) C H 3 O H & ( ^ X c ><J (B) PhOH &[0 OPh

II
0
o
OH II
K
(C) PhOH & HO. (D) CH 3 OH & [ O C-CH3
o
C- C-CH3
II
o
V- lo
Q. 47 m-Aminophenol on treatment with NaOH and C 0 2 gives which of the following as major product?
COOH
H, OH f ^ Y ° H
(A) (B) L J (C)

XOOH(D)^Y^COOH
COOH NH,
OH
Question No 48 to 50 (3 questions)
500°C •No reaction
LiAlH4
Na BH ,
COOH
Q.48 Compound 13'is?
(A)' (B) ^ J - C O O H (C) ^ e ^ - C H 2 - O H ( D) ( ^ T n j h c i i j
Q. 49 Organic compound A does not undergo de carboxylation reaction because?

(A) Intermediate does not follow Saytzeffn rule
(B) Intermediate does not follow Hofmanris rule
(C) Intermediate does not follow Bredict's rule
(D) Intermediate does not follow MarkwoniKoffs rule
Q. 50 Total No. of stereoisomers of B are?
(A) 2 (B)4 (C)3 (D)6
EXERCJSE-I(B)
Q. 1 Compound which gives alcohol on reduction is/are 0 0
•II II
(A) Me - C - CI (B) Me -C -N H, (C) Me -C H- CH 2 (D) Me -C -O C- Me
II II "
O o
Q.2 Phenol and ethanol are distinguished by the reaction with
(A) Red litmus (B) NaHCO, (C) FeCl3 (D)NaOH
H2 d l
Q. 3 In the reaction sequence, CaC2 ° >A ' B — C , true about the product C is
(A) give yellow ppt. with NaOI (B) itsfinaloxidation product is carbonyl compound
(C) itsfinaloxidation product is C0 2 and H 2 0 (D) itsfinaloxidation product is CH3COOH
Q.4 Which can be cleaved by HI0 4 ?

0 0 OHO
II II I H
(A) CH3CH 2CCH 2CCH 3 (B) CH3CHCCH2CH3
0 0
(C)
, ,
y— / , (
11 11
(D) CH 3CCH 2CHCH2CCH 3
OH ''OH \qh
Q5 HBO, oxymercuration-demercuration and acid catalysed hydration will not give same product in
(B)
O (cO (dO
Q. 6 Diethyl ether reacts with PCP5 to form
(A) Ethyl chloride (B) Phosphorous oxy trichloride
(C) Ethenol (D)Ethene
[13]
fe Bansal Classes Alcohols & Ethers
Q.7 Select the correct synthesis products
(D) ( C ^ B r + (CH3)3CONa > (C H3) 3 CO-ô)
Q.8 The molecules of ether dehydrates in the presence of-

(A)A12 0 3 (B)H 3 P0 4 (C)H2S 2 0 7 (D) liq. NH 3
Q.9 Anhydride of alcohol is

(A) Ether (B) Aldehyde
(C) Alkyl hydrogen sulphere (D) Alkene
Q. 10 Lucas test is used to make distinction between 1°, 2° and 3° alcohols

R O H + HC 1 anhydrous ZnCl 2 > R C j | + H 2 0
c0nc
- White turbidity
This shows that

(A) ROH behaves as a base
(B) greater the value of pKa (alcohol), greater the reactivity with conc. HC1 and thus sooner the formation
ofwhite turbidity.
(C) alcohol which reacts fastest with Na metal, will give turbidity at fastest rate
(D) alcohol which gives red colour during Victor Mayor test, will give turbidity at slower rate then those
giving blue or white colour during Victor Mayor test.
Q. 11 If ethanol dissolves in water, then which ofthe following would be done

(A) Absorption of heat (B) Emission of heat
(C) Increase in volume (D) Contraction in volume
Q. 12 Which method is useful for the synthesis of ether?
(D) (CH3 )3 CBr + CH3 CH 2 ONa •
Q.13 Which of the following can react with TsCl

(A) Glycerol (B) Oximinoacetone
(C) Oil ofwintergreen (D) dimethyl amine
(!§Bansal Classes Alcohols & Ethers [U]
Q. 14 Which is/are correct statements?

CH 3 CH 3
\ / CH 3 OH
(A) H2S 4
H
/Urn
0 T CH 3
°
nucleophile attacks here when epoxv linkage is cleaved
CH; CH;
rm \ /
(D J ,\~ ~K CH,OH
H | O CH 3
nucleophile attacks here when epoxy linkage is cleaved
O /
(C) This is only affected in reduction to 2° alcohol
O
" H+
(D) R-CÔH + Ht O-R
I
These bonds undergo cleavage in the reaction
Q.15 3 -methyl-3 -hexanol can be prepared by

(A) CH3MgI and 3-hexanone, followed by hydrolysis
(B) C2H5MgI and 2-pentanone, followed by hydrolysis
(C) C3H7MgI and 2-butananone, followed by hydrolysis
(D) C4H9MgI and propanone, followed by hydrolysis
Q 16 In which cases product formed are not according to reaction?
(A) ^ ^ - O H + HNO3 h
2
s
°4 >
•NO,
0 H
(B) ( ^ y ~ +HN0 3 h
2s°4 ? Q-ONO.
(C) CH2 = CH-CHO + LiAlH4 —-> CH3 CH,CH2OH
(D) ~ -Cl + CH3ONa > -OCH
Q.17 Dehydration of alcohols take place more rapidly with POCl than with H,S0 . Select the correct
3 4
statement(s) about the following dehydration reaction.
Is. j ) pyridine
(A) It does not involve carbocation. *

(B) It involves R-OPOC1, with - OPOC1, as a better leaving group.
(C) It involves E2 mechanism as pyridine base abstracts proton from the adjacent carbon as the same
time at which - OPOCl2 is leaving.
(D) It is E1 reaction without formation of carbocation.
Q.18 Which of the following will get oxidised by Br 2 / KOH into carboxylic acid?
(A) CH3-CH2-OH (B) CH - CH3
OH
(C) ( ^ y - C H 2 O H (D) Q S
<
CII,
Q. 19 In Kolbe-Schmidt reaction, o-hydroxy benzoic acid is predominantly formed. This is because

(A) salicylate anion is a stronger base than phenoxide ion
(B) salicylate anion is a weaker base than phenoxide ion
(C) p-hydroxy benzoate ion is a stronger base than phenoxide ion
(D) p-hydroxy benzoate ion is a stronger base than salicylate ion
Q. 20 Methanol can be distinguished from ethanol by

(A) Heating with I2 and alkali (B) Treating with schifFs reagent
(C) Treating with Cr03 solution in dil. HjSO,^ (D) Treating with Lucas reagent
Q.21 Products form by following reactions are

OH
A.
CH,
OH OH
OH
CHO
C A ) ^ ( B ) ^ c h o (C) ^ .(D)
CH3 CH3 C H 3 CH O CH
Q .22 For the reactions shown below, identify the correct statements) with regard to the products formed:
ph
(i) *>\y0 p (h) ph
^\7°
(A) P and Q are identical

(B) P is recemic and Q is optically active
(C) P and Q are positional isomers
(D)hoth are optically active
Tilden NH
Q.23 C,NSNH, > (i) ? > (ii) (iii). The product (iii) can be
reagent HC1
(A) Alcohol ' (B) Ether (C)Alkyl chloride (D) Alkyl nitrite
Q 24 Products form during dehydration offollowing alcohols are
(A)f ] (B)( ) (C) | (D)
Q. 25 Consider the following compound A (below)

.OH
\ /
cy \>H
O
Select the correct statement(s)
(A) It is more acidic than CH3OH (B) It is more acidic than CH 3 COH
(C) It reacts very fast with Lucas reagent (D) It is a diacid base
Q. 2 6 Match the following:

Reaction Mechanism
OH
(A) (P) change in number of carbon in cycle
CH=CH? "
CH 2 ~OH
(B) OH (Q) Pinacol rearrangement
CH3CH3
3 H ®
(C) OH > (R) Oxidative bond cleavage
heat
O-CH,
<P) (S) Ketone as product
Q. 27 Match the column:

Column I Column II
(A) Identification of 1°, 2°8c 3° Alcohols (P) Oxymercuration demercuration
(B) Identification of 1°, 2°& 3° Nitro alkanes (Q) Cu/300° heat
(C) Formation of alcohol by anti Markovnikov's (R) Victor Mayer's test
addition ofH 2 0
(D) Formation of alcahol by Markovnikov's (S) Hydroboration oxidation
addition
(i) Lucas test
& Bansal Classes Alcohols & Ethers [14]
Q.28 Match the column:

Column I Column H
(A) Oxidation of 1 ° alcohol in aldehyde (P) KMn0 4 /A
(B) Cr0 3 L U .HC1 (Q) Collin's reagent

N'
(C) Cr0 3 .2 (R) Jone's reagent

N
(D) Oxidation of alkene into acid (S) P.C.C
Q.29 Match the products offollowing: .

Column I Column II
(A) < 0 > 0 - C , 2 ^ 0 > (?) (0>i

(B) Violet color is obtain by the (Q) { o > CH
2 - OH
reaction of neutral FeCl3 with
(C) Reaction ofbenzaldehyde with (R) OH
LiAlH 4 /H 2 0 gives
(D) f n l + K i — > ? (S) <OVCH2-I
Q.30 CH, - CH
I
- CH = CH 2 ReageatR^ Alcohol
CH 3
which is true about alcohol and R?
Alcohol Reagent
(A) CH , - CH - CH 2 - CH 2 OH B 2 H 6 , H2 0 2 /Na0H
"•I
CH,
CH3-CH-CH^CH3
(B) I I PdCl2, H 2 0, 0 2 / LAH
CH 3 OH
OH
(O CH 3 - - C - C H 2 C H 3 Hg(OAc)2 HÔ / NaBH 4
CH 3
OH
(D) CH3 - C - C H2 CH3 dil. H2S0 4
CH 3
EXER CISE-II
Q. 1 What reagents could you use for the following conversions

(a) MeC0(CH 2 ) 0 C0 2 Et -> MeCH0H(CH 2 ) 2 C0 2 Et
(b) H0 2 C ( C H 2 ) 4 " C 0 C r - > H0 2 C - ( C H2 ) 4 CH20H
(c) 0 2 N(CH 2 ) 2 CN -> 0 2 N(CH2) 2 CH 2 NH 2
(d) 0 2 N( CH 2 ) 2 CH = CH 2 -> H2N(CH2 )2 CH=CH2
(e) Me2 CHCOCl -> Me 2 CHCHO
(f) 0 2 N(CH 2 ) 3 CH0 0 2 N(CH2) 3 CH 2 OH
(g) 0 2 N( CH 2 ),CH=CH 2 -> 0 2 N( CH 2 ) 3 CH 3
Q.2 Following compounds undergoes reaction with Mn0 2 . What are the products in each case?
(a) CH 3 CH 2 CH=CHCH20H (ty PhC IÔ H (c) PhCH(OH)CH2 CH 2 OH
(d)MeCH=CH(CH 2 ) 3 OH (e) [ ^ > - O H
Q. 3 Carry out the following conversion

C H 0
(i) / v
Br
-»
MeO' /CHO
© Acraldehyde Glyceraldehyde
(iii)
Br - CH, CHO Ph CHOH CH 2 CHO
O
(iv)
CO,Et -CH 2 OH
(v) C H 2 - C H 2 CHO Glyceraldehyde
CI
Q. 4 Outline a mechanism to account for different isomer formed when Me 2 C CH 2 reacts with CH3 OH
N /
o
in acidic and in basic medium.
Q. 5 Find the structures ofA to F.

mild
•D ^ ^ C I L C O J I
C6H12 0
(A)
Q.6
Product
Explain product formation. H ow two OH groups behave differently.
Q.7 R2 C = O + Et 3 Al -> C 2 H 4 + R 2 CHO AlEt2

Suggest a mechanism for the reaction.
OH
Q.8 TsCl What are A to E?

Pyridine
NaBr
Mg
dry ether •D-S2-B
1.CHJCHO
2. HjO
Q. 9 Identify A to E in the Mowing reactions.
H+
(i) Me 2 CO+A Me2C.
\
o-J
© MeCHO + HOCH2 CH2 SH
(i)
1 .HCO3H
(iv)
2.H20
Q. 10 What are the order of rates of oxidation with HI0 4 of the following diols. Explain with reasons.
(a)Me 2 C(0H)C(0H)Me2 (b) Me2C(OH)CH (OH) Me
(c) CH2(OH) CH2 (OH) (d) Me CH(OH) CH (OH) Me
Q. 11 t- Butanol in presence offenton's reagent forms 2,5 dimethyl hexane 2,5 diol as one of the product.
Explain with the mechanism.
Q. 12 How you distinguish the following compounds?

(a) t butyl alcohol & n butyl alcohol
(b) ethyl alcohol & n propyl alcohol
(c) allyl alcohol & n propyl alcohol
(d) benzyl methyl ether & benzyl alcohol
Q.13 Differentiate:
(a) 1 -Hexanol and 1 -chlorohexane (b) Diethyl ether and n-butanol
(c) Diethyl ether and n-pentane
Q.14 Explain:
(a) No est erifi cation takes place between ethyl alcohol and excess of sulphuric acid at 170°C.
(b) Sodium chloride solution in water is added to decrease the solubility of organic compounds in water.
Q.15 Predict A, B & C.
CH3OH - P +L2
>A +C
Q. 16 Carry out conversion of methyl alcohol into ethyl alcohol and vice versa.
^Bansal Classes Alcohols & Ethers PV
Q.17 Arrange the compounds (i) Ethanol, propane and 1-pentanol, (ii) Butane 1,2,3-pentanetriol and butyl
alcohol, (iii) Pentane, 1 -pentanol and 1 -hexanol, on the basis of(a) in order of increasing boiling points
and (b) in order of increasing solubility in water.
Q.18 Complete the following equations & comment:
(iii) Me2C = CH2 ^ ^ o >?
pressure
Q. 19 Complete the following equations:
(i) n - C3H7 - C0 2H > n - C4H9OH
H+
(ii) Me2CO + EtMgl •? >?
(iii) EtC02Et + 2MeMgI >? >?
T T
(iv) (^ / /=CHC0 2Et
/=CHCO,Et — ™T™
— >—^\ = C^=CHCH T
2OH
Mn0?
Q. 20 t-butyl alcohol reacts less rapidly with metallic sodium than the primary alcohol. Explain why?
Q. 21 Diethyl ether behaves as base. Why?
Q. 22 What is the significance of proof spirit?
Q. 23 Sodium metal can be used for drying diethyl ether but not for ethanol. Why?
Q.24 Sometimes explosion occurs during distillation of ether sample. Give the reason.
Q. 2 5 Ethyl alcohol is denatured with methyl alcohol. Why?
2 4
Q.26 C2H5I — A - >B
Ag20
Q. 27 Ethyl alcohol reacts with HI but not with HCN. Explain why?
Q. 2 8 Write the structure ofthe principal organic product formed in the reaction of 1 -propanol with each of the
following reagents:
(i) Potassium dichromate (K2Cr 207) in aqueous sulfuric acid, heat
0
(ii) II in the presence of dissolved hydrogen chloride.
Acetic acid CHXOH
(iii) CH3 y~S0 2 Cl in the presence of pyridine
OO
(iv) C6H5COCC6H5 in the presence of pyridine
m
(v) Presence pyridine
Q. 29 Complete the following series of equations by writing structural formula for compounds A through I:
NaHC
(a) ^\\ J j// —HCl
C 5 C ?HCf J1
H °3 ) C H O ^ ^ > C5 H 6 O
\\ // > S 7 ^ 5 8 H2S04,H20
Compound A Compound B Compound C
SOC 2 Na B 4
(b) CH, = CHC H,C H,C HCH , ' > C,H,,C1 — ^ >r HXIO " >C«H,,(
1 pyridine 5 5 11
I (ii)Zn/H20 ^
OH (D) (E) (F)
(c) ^ ^ N ^ P H > Compound G — Compound H > Compound I

* ' ' ' CH, C1,
e.
heat
Q. 3 0 Predict the principal organic product of each of the following reactions. Specify stereochemistry where
appropriate.
/Br
(a) - ^ ( A )
methanol
H;C
CH 3 H
(b) I | > + CH3 ONa ° >(B)
CH2C6H5
(c) ( VC H- CH 2
W V
(d) CH3(CH 2 ) 16 CH 2OTs + CH 3 CH 2 CH 2 CH 2 SNa > (D)
Q. 31 Deduce the identify of the missing compounds in the following reaction sequences. Show stereochemistry
in parts (b) through (d).
(a) CH2 = CHCH2Br compound A(C4HgO) > compound B(C 4 H g Br 2 0)

( i i i ) H , 0+ g
DC
compound D < compound C (C4 H7BrO)
COoH
(1)
(b) Cl- —H ™4 > compound E (C3H7C10) K0H H
' 2° > compoundF (C 3 H 6 0)
CH, '
^Bansal Classes Alcohols & Ethers [19]
Q. 3 2 Choose the reaction in each ofthe following pairs that proceeds at the faster rate. Explain your reasoning.
(a) Base-promoted hydrolysis of phenyl acetate or m-nitrophenyl acetate
(b) Base-promoted hydrolysis of m-nitrophenyl acetate or p-nitrophenyl acetate
(c) Reaction of ethyl bromide with phenol or with the sodium salt of phenol.
(d) Reaction of ethylene oxide with the sodium salt of phenol or with the sodium salt of p-nitrophenol
(e) Bromination of phenol or phenyl actetate.
Q. 3 3 Explain why ArOR ethers are cleaved to give RI and ArOH rather than Arl and ROH.
Q.34 Explain the mechanism offollowing:
(iii)
(iv)
R' R
0-CH 7 -CH=CHR OH CH 2 -CH=CHR

CH=CH-CH3 CH=C-CH 3
(v)
Me
0 35 Outline a synthesis ofeach alcohol from the indicated starting materials:
(a) Isopropyl alcohol from a hydrocarbon (b) n-butyl alcohol from acetylene
(c) allyl alcoholfrompropane, and (d) t-butyl alcohol from t-butyl chloride
Q.36 What product is expectedfromthe reaction of (f O with (a) LiAlH4 and (b) H^/Pt
Q.37 Give the product of the reaction of PhjCHC^ OH with HBr and explain its formation.
Q.38 Give the product and write a mechanism for the acid dehydration ofcyclobutylcarbinol.
PC 5 KCN
Q.39 C2H5OH ' > (A) - > (B) - ->(C) ->(D) •(E)
Q.40 CH3CH2CH20H (A) ->(B) + (C)
EXERCISE-III
Q. 1 Compound (A) gives Lucas test within 5 minutes. 6g (A) when reacts with Na, 1120 mL of H2 is
generated at STP. fA) having one oxygen per molecule. What is the structural formula of(A)? Compound
(A) when treated with PBr3 gives (B) which when treated with benzene in presence of anhydrous A1C13
gives (C). What are (B) and (C)?
Q.2 An open chain compound (A) C5HgO is optically active. When (A) is hydrogenated in presence of Pd
as catalyst, it absorbs two moles of F^ per mole of (A) to produce compound (B) C5 H 12 0 which is
optically inactive. However when (A) is warmed with dilute E^SC^ in presence of HgS04 it gives
compound C(C5H10O2) which is still optically active. C responds to iodoform test. What are the structures
of A to C?
Q .3 An organic compound (A) C10H12O gives red colour when treated with cerric ammonium nitrate & also
decolourises Br2 in CC14 to give B (C10H12OBr2). A can show both geometrical & optical isomerism. A
on treatment with L, & NaOH gives iodoform & an acid (C) after acidification. Give the structures ofA
to C & also the stereoisomers of A.
Q. 4 A(C7H]4) decolorises Br2 in CC14 reacts with Hg(OAc)2. THF-NaBH4 to form B (resolvable compound)
A———» C < K M n Q ^ - 3 hexanol
2.Zn/H20
l .B 2 H 6 . TH F v
> YMaD
D (isomer of A) 2 H 0 / 0H - E (chiral) ^ > F (chiral carboxylic acid)
D (isomer of A) 1
°3 > G < KMn0 4 /alkaline 2 m e t h y l 3 p en tanol
2.Zn/H20
Find out A to G.
Q. 5 Suggest short, efficient reaction sequence suitable for preparing each ofthe following compounds from
the given starting materials and any necessary organic or inorganic reagents.
(0 CH2OCH3 from - COCH, (ii) frombromobenzene and cyclohexanol
(iii) C6H5CH2CHCH3 frombromobenzene and isopropyl alcohol

I
OH
(iv) CfiH5CH2CH2CH2OCH2CH3frombenzyl alcohol and ethanol.
(v) from 1,3-cyclohexadiene and ethanol
(vi) C6H5CHCH2SCH 2CH3fromstyrene and ethanol

I
OH
Q.6 A compound (X) reacts with thionyl chloride to give a compound (Y). (Y) reacts withMg to form a
Grignard reagent, which is treated with acetone and the product is hydrolysed to give 2-methyl-2-butanol.
What are structural formulae of (X) and (Y)?
Q. 7 The compound (D) reacts with BH 3- Tetrahydrofuran and then alkaline H 2 0 2 to give chiral (E). Oxidation
of (E) with KMn0 4 (acidified) gives a chiral carboxylic acid (F). Ozonolysis of 'D' gives after reduction
with Zn the same compound (G), which is obtained by oxidation of 2-methyl-3 -pentanol with acidified
KMn04. Identify (D), (E), (F) and (G).
Q. 8 An organic compound (A) contains 60.12% Carbon, 13.13% Hydrogen and has vapour density 3 0. On
oxidation it gives (B) C3 H 6 0 which on further oxidation by NaOH +12 produces a salt of the acid (C)
C2H402. When (B) is treated with hydroxyl amine, a compound of molecular formula C3H7NO (D) is
formed. What are (A), (B),(C) and (D)?
Q. 9 Compound (A) C 4 H |0 O reacts rapidly with metallic sodium, but undergos almost no reaction with
Lucas reagent. When (A) is treated with hot concentrated sulphuric acid, a new compound (B) C4H8 is
formed. If C4Hg is hydrated with sulphuric acid a new compound (C) C4H9OH is formed, which is
almost inert to metallic sodium but reacts rapidly with Lucas reagent. What are (A), (B) and (C)?
Q. 10 A compound (X) containing C, H and 0 is unreactive towards sodium. It does not add bromine. It does
also not react with Schiffs reagent. On refluxing with an excess ofHI, (X) gives only (Y). (Y) on hydrolysis
gives (Z) which can be converted to (Y) by the action of P +12, Compound (Z) on oxidation gives an
acid of equivalent weight 60. What are (X), (Y) and (Z)?
Q. 11 A compound (A) C; Hlf ) n^ yields on acetylation (B) offormula C12 H18 08. How many hydroxyl groups
are present in compound? A l s o write structures of (A) and (B).
Q. 12 An optically active alcohol (A) (C6H10G) absorbs two moles of hydrogen per mole of (A) upon catalytic
hydrogenation and gives a product (B). The compound (B) is resistant to oxidation by Cr0 3 and does
not show any optical activity. Deduce the structures of (A) and (B).
Q.13 An unsaturated hydrocarbon (A) on hydration gave alcohol (B). Oxidation of (B) gave a ketone (C).
When the hydrocarbon (A) was submitted to ozonolysis it gave formaldehyde and acetaldehyde. What
one formula would you assign to A, B and C? Give the reactions involved.
Q. 14 Compound (A) reacts with sodium to liberate H2 forming a compound (B). When (A) is treated with
HC1 + ZnCl2, an immediate reaction takes place liberating (C). When (A) is heated with H 2S0 4, (D) is
formed. Ozonolysis of (D) gives a three carbon ketone and another isomeric compound. What are (A),
(B), (C) and (D) ?
Q.15 An organic compound (A) (C4H]0O) reacts with HI giving a compound (B) (C4Hgl) which on reduction
gives a normat hydrocarbon having four carbon atoms. On oxidation A gives compound (C) (C4HgO)
and then an acid (D) (C4H802). Deduce th§ structures of, B, C and D giving reasons.
Q. 16 An organic compound (A) gives hydrogen on reacting with sodium. It also gives iodoform test and forms
an aldehyde of molecular formula (B) (C2H40) on oxidation. Name the compound (A) and (B).
Q.17 An organic compound (X) on analysis gives 24.24% C, 4.04%H. Further sodium extract of 1.0 g of (X)
gives 2.90 g ofAgCl with acidified AgNO, solution. The compound (X) may be represented by two
isomeric structures (Y) and (Z). (Y) on treatment with aqueous KOH solution gives a dihydroxy compound,
while (Z) on similar treatment gives ethanal. Find out (X), (Y) and (Z).
Q.18 Compound (X) (C5HgO) does not react appreciably with Lucas reagent at room temperature but gives
a precipitate with ammonical silver nitrate. With excess ofMeMgBr, 0.42 g of(X) gives 224 ml CH4 at
STP. Treatment of (X) with H2 in presence of Pt catalyst followed by boiling with excess HI gives
n-pentane. Suggest structure for (X) and write the equations involved.
Q. 19 An alcohol (A) when heated with concentrated H^SC^ gives an alkene (B). When (B) is bubbled through
bromine water and the product obtained is dehydrohalogenated with excess of sodamide, a new
compound (C) is obtained. The compound (C) give (D) when treated with dilute H^SC^ in presence of
HgS04. (D) can also be obtained either by oxidising (A) with KMn04 orfromacetic acid through its
calcium salt. Identify (A), (B), (C) and (D).
Q. 20 Compound (A) contains only carbon and hydrogen. It decolorizes bromine in CC14 solution and reacts
slowly with concentrated HjSO^ Compound (A) reacts withHBr to form (B). (B) reacts with NaOH
to form (C). (C) on oxidation gave hexanone-3. Write structures of (A), (B) and (C).
Q. 21 A hydrocarbon (A) (molecular formula C5HJ0) yield 2-methylbutane on catalytic hydrogenation. (A)
adds HBr in accordance with Markownikoff s rule to form a compound (B), which on reaction with
silver hydroxide forms an alcohol (C) C5H12 0. Alcohol (C) on oxidation gives a ketone (D). Deduce
(A) to (D) and give the reactions involved.
Q.22 (A) (Vb ) . _JiM_> ( c) V

(^-WkÂ)
' 250°C > (ii)AgOH ' 150°C ' ( i i ) H 2 0 2 ,0H- '
In the above reactions scheme (A) and (C) are isomers. (B) has a formula of C5H10. (C) Can also be
obtained from the product of the reactions of CH3CH2MgBr and (CH3)2CO. Give structures of (A),
(B)and(C).
EXERCISE-IV (A)
Q.l l O j + C 02 — > x -J*"-* T c n n H ; The product X in the reaction is:
[REE 1990]
w(OJ <B)(OJ (O^J (D )g l C0 0N i

Q.2 The products of combustion of an aliphatic thiol (RSH) at 298 K are: [JEE 1992J
(A) C02 (/), H 2 0 (g) and S02 (g) (B) C0 2 (g), H 2 0 (g) and S0 2 (g)
(C) CO2(l), H 2 0 (I) and S0 2 (g) (D) C0 2(g), HÔ (I) and S0 2 (/)
Q. 3 An organic compound C 3 H 6 0 does not give aprecipitate with 2,4-dinitrophenyl hydrazine reagent and
does not react with sodium metal. It could be: [JEE 1993]
(A) CH3-CH 2-CHO (B) CH 3 -CO-CH3 (C) CH2=CH-CH2OH (D) CH2= CH-OCH3
A
Q .4 The reaction products of C6H5OCH3 + HI > are: [JEE 1995]
(A) C6H5OH + CH3I (B) C6H5I + CH3OH (C) C6H5CH3 + HOI (D) C6H6 + CH3OI
Q5 The order of reactivity of the following alcohols: [JEE 1997]

CH 3 CH 3
CH 3 / V CH3
F o nI 0 H
Y
OH
Ph
(IV)
OH
U) (II) an)
towards conc. HClis:
(A) 1 > II > III > IV (B) I > III > II > IV (C) IV > III > II > 1 (D) IV > II > III > I
Q.6 .Among the following compounds, the strongest acid is: [JEE 1998]
(A) HC=CH (B)C 6H6 (C) C2H6 (D) CH,OH
Q.7 Benzenediazonium cliloride on reaction with phenol in weakly basic medium gives: * [JEE 1998]
(A) Diphenyl ether (B) p-hydrooxyazobenzene
(C) Chlorobenzene (D) Benzene
Q. 8 Which one of the following will most readily be dehydrated in acidic condition: [JEE 2000]
O O
A0 AOH OH
cb) A XYX
A
/ V \ / V \ 0 H 0 H
Q.9 1 -propanol & 2-propanol can be best distinguished by: [JEE2001]

(A) Oxidation with alkaline KMn04 followed by reaction with Fehling solution
(B) Oxidation with acedic dichromate followed by reaction with Fehling solution
(C) Oxidation by heating with copper followed by reaction with Fehling solution
(D) Oxidation with concentrated H2 S0 4followedby reaction with Fehling
Q. 10 Identify the correct order ofboiling point ofthe following compounds: [JEE 2002]
CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH 2 CHO CH 3 CH 2 CH 2 COOH
1 2 3
(A) 1 > 2 > 3 (B) 3 > 1 > 2 (C) 1 > 3 > 2 (D)3>2>1
O N a + ( e xc e s s )
Q. ll < O ^ O H + C 2 H5 I — ^ [JEE 2003]
; OH(anhydrous)
(A) < 0 } - O C 2 H 5 < B ) @ - I (C)C 6 H 5 OC 6 H 5 (D)C 2 H 5 OC 2 H 5
Q. 12 Reaction of entainomerically pure acid with 1 chiral carbon and racemic alcohol with 1 chiral carbon
gives an ester which is: [JEE 2003]
(A) Meso (B) Optically active mixture
(C) Racemic mixture (D) Enantionmerically pure
Q.13 On acid catalysed hydration, 2-phenyl propene gives: [JEE 2004]

(A) 3-phenyl-2-propanol (B) 2-phenyl-1 -propanol
(C) 1 -phenyl-3 -propanol (D) 2-phenyl-2-propanol

Q. 14 Phenyl magnesium bromide reacting with t-Butyl alcohol gives [JEE 2005]
CH, /CH3
(A) Ph - OH (B) Ph-H (C) Ph-0-C~C:H 3 ( D ) PI1-C-CH3
CH \ CH,
Q.15 Which is the best reagent to convert cyclohexanol into cyclohexene. [J EE 2005]
(A) conc. HC1 (B)con c. HBr (C) conc. H 3 P0 4 (D)H Cl + ZnCl2
CH3H CH 3
Q. 16 Compound (X) C H 3 0 - < ^ O y > is reacted with aqueous acetone it gives
H CI CH 3
following products:
CH3H CH 3 CH3H CH 3
CH3O-< O) -<Q> NO2(K) CH 3 O-^> - ^ ( O ) - N 0 2 (L)
H OHCH 3 OH H CH 3
CH3H CH 3
CH 3 O- -N0 2 (M)
H CH 3 OH
(A) K, L (B) K, M (C) L only (D) M only [J EE 2005]
^Bansal Classes Alcohols & Ethers [25]
Q 17 + CI - CH 2 CH 2 - CH 3 ^ ^ > Q + Phenol [JEE 2006]
The major products P and Q are
( A ) j ^ a n d C H 3 C H 2 CH O (B) j ^ j and CH 3 COCH 3
(C)fSandCH 3COCH3 (D) f S and CH3 CH 2 CHO
feBansal Classes Alcohols & Ethers
EXER CISE-IV (B)

OA When t-butanol and n-butanol are separately treated with a few drops of dilute KMn0 4 in one case
only, purple colour disappears and a brown precipitate is formed. Which of the two alcohols gives the
above reaction and what is the brown precipitate? [JEE 1994]
(XZ 3,3-Dimethylbutan-2-ol losses a molecule of water in the presence of a concentrated sulphuric acid to
^ give tetramethyl ethylene as a major product. Suggest a suitable mechanism. [JEE 1996]
Q.3 A compound
filtrate D (CgH10O)
on acidification upon
gives treatment
a white solidwith (C7H602solution
(E) alkaline ). Writeofiodine
the structures a yellow
givesof (D) andprecipitate. The
(E) and explain
the formation of (E). [JEE 1996]
Q. 4 Which of the following is the correct method for synthesising methyl-t-butyl ether and why?
(i) (CH3)3CBr + NaOMe > (ii) CH3Br + tert-BuONa > [JEE 1997]
O = C-OH HOCH2
Q.5 I + I [JEE 1997]
O = C-OH HOCH2
Qj / Discuss why o-hydroxy benzaldehyde is a liquid at room temperature while p-hydroxy benzaldehyde is
a high melting solid? [JEE 1999]

Q.7 White the structures of the product A&B [JEE 2000]
CH
n -C-0 1 8 C H h
3°® .
3 ^ u ^2 n 5 2
> A+B
O
Q.8 Cyclobutyl bromide on treatment with magnesium in dry ether forms an organometallic A. The
organometallic reacts with ethanal to give an alcohol B after mild acidification. Prolonged treatment of
alcohol B with an equivalent amount ofHBr gives 1 -bromo-1 -methylcyclopentane (C). Write the structures
ofA, Band explain how C is obtained from B. [JEE 2001]
Q. 9 Identify X, Y and Z in the following synthetic scheme and write their structure. Explain the formation of
labelled formaldehyde (H2C*0) as one of the products when compound Z is treated with HBr and
subsequently ozonolysed. Mark the C* carbon in the entire scheme. [JEE 2001]
BaC*03 + H 2 S0 4 > X (gas) [C* denotes C14]
CH2 - CH - Br ^ M * /eth er >y LlAm

-* >Z
+
(ii)X,(iii)H,0
Q.10 Mention two esters produced when a racemic mixture of 2-phenyl propanoic acid is treated with (+)
2-butanol. What is the stereochemical relationship between these esters? [JEE 2003]
Q. 11 An organic compound P(C 5H10O) Reacts 1015 times faster then ethylene with dil.H2S04 to give two
products Q and R. Both Q and R give positive iodoform test. Identify P, Q and R and also give reason
for very high reactivity of P. [JEE 2004]
Q. 12 (X) C5H!3N NaNo2 ,HCi >( Y) (Tertiary alcohol + other products)

-N2
(Optically active)
Find X and Y. Is Y optically active? Write the intermediate steps. [JEE 2005]
ANSWER KEY
EXER CISE-I(A)
Q.I- B Q.2 A Q3 C Q.4 B Q.5 B Q.6 D Q.7 D

Q.8 C Q.9 D Q.10 c Q.ll A Q. 12 C Q.13 A Q.14 C
Q.15 B Q. 16 A Q.17 B Q.18 C Q. 19 D Q.20 C Q.21 D
Q.22 A Q.23 B Q.24 D Q.25 A Q.26 B Q.27 A Q.28 B
D Q.34 D Q.35 D
Q.29
Q.36 A
B Q.30
Q.37 A
A Q.31
Q.38 C
B Q.32
Q.39 C
A Q.33
Q.40 A Q.41 C Q.42 A
Q.43 A Q.44 D Q.45 A Q.46 C Q.47 C Q.48 C Q.49 C
Q.50 A
EXER CISE-I (B)
Q.l A,C,D Q.2 C Q.3 A,C Q.4 B

Q.5 A, B,D Q.6 A,B Q.7 A,B,C Q.8 A,B,C
Q.9 A,D Q.10 A,B,D Q.ll A,C Q.12 A,B,C
Q.13 A,B,C,D Q.14 AB,C,D Q.15 A,B,C Q.16 A,C,D
Q.17 A,B,C Q.18 A,B Q.19 Q.20 A
Q.21 A,C Q.22 C ,D Q.23 A,B,C,D Q.24 A,B,C,D
Q.25 A,B Q.26 (A) P, Q, S; (B) R,S; (C) P; (D) S
Q.27 (A) Q,R,T, (B) R, (C) S, (D) P Q.28 (A) Q,R,S (B) S (C) Q (D) P
Q.29 (A) R, S; (B) R; (C) Q; (D) P Q.30 A,B,D
EXER CISE-II
O
Ii
Q2 (a) Et-C H=CH-CHO (b) Ph- CHO (c) Ph - C - CH 2 - CH 2 - CH
(d) No reaction (e)
OCH3 OCH 3
Q. 4 In acidic medium Me 2 - C - CH 2 and In basic medium Me 2 C - CH 2
OH O®
Q.5 (A) C H3 - C -O - C -C - C- C , (B ) C H r C H 2 OH, (C) CH 3 - C H 2 - C H 2 - C H 2 - O H ,
O OH O
II i • II
(D) C H , - 0 - H , ( E ) C H 3 - CH - C H - C H O (F) CH - C H = C H - C - H
faBansal Classes Alcohols & Ethers [28]
Q. 9 (A ) = C H 2 - O H
I
C H 2 -OH
Q.10 a > b > d > c
Q. 12 (a) Lucas reagent (b) Iodoform (c) PBr 3 & AgN0 3 (d)Na
Q. 13 (a) 1-hexanol reduces organ red Cr0 3 to greenCr3^ while 1-chlorohexane gives white ppt. ofAgCl on
warming with ethanolicAgN03. \
(b) n-Butanol gives a positive test with Cr0 3 in acid and evolves H2 with sodium: while dry ethyl etheris
negative to both tests
(c) Unlike n-pentane, diethyl ether is basic and

+
dissolves in conc. f^SC^
(C 2H5)20 + H ^ > (C 2H5)2OH + HSO"
Q.14 (a) Ethyl alcoholfirstreacts with sulphuric acid to form ethyl hydrogen sulphate which readily lo ses a
molecule of sulphuric acid when heated with concentrated sulphuric acid at 170°C to form ethylene,
(b) When sodium chloride is dissolved in water it reduces the polarity of water the space between water
molecuules are occupied by sodium and chloride ions with the result the solubilty of the organic compound
is reduced.
Q.15 CH3I, CH 3 -0-CH3 , CH3I
Q.1 6 CH OH p+12 CH,I KC N CH CN reduction CH CH NH HONO
3 ) ? 3 ) 3 2 2 ?
Methanol
CH3CH2OH _JO)_> CH3CQOH

Ethylamine Ethano!
C1
CH3OH ( KOH(aq.) CHGCL ( 2 ' CH,
Q.17 (a) In order of increasing boiling points:
(I) Propane < Ethanol <Pentanol-l
(ii) Butane < Butyl alcohol <1,2,3-Pentanetriol
(iii) Pentane < 1 -Pentanol < 1 -Hexanol
The explanion is based on molecular weight and hydrogen bonding
(b) In order ofincreasing solubility in water:
(i)
(ii) Propane<<butyl
Butane
Pentanol-1 <Ethanol
alcohol < 1,2,3-Pentanetriol
(iii) Pentane < 1 -Hexanol < 1 -Pentanol
The explanation is based on hydrogen bonding
Q.18 (i) MeOEt + HI ^ l®MeÔ-Et—> Mel + EtOH — > EtI

The reaction is SN2 the smaller group forms the iodide (steric effect) & stops at thefirststage in the cold.
When heated, the reaction proceeds to the second stage.
(ii) Et2 0 — » N o reaction as there is no active H in the compound.
H
h s
(iii)
W
Me, = CH, 2 °4- h2° > M e 3C +
Me3C H
°
re ss ur e
> Me 3 C-0-CMe
+
3 "H+ >Me3 3C-0-CMe33
pressure P
Q. 19 (i) n - C3H7C02H > n - C4H9OH

or B 2 H 6
/OMgl
H+
(ii) Me2CO + EtMgl >M 2 C<^ E t > MeXCOH)Et
IMgOx / M e
(iii) EtC02Et + 2MeMgI > C "2° ) EtCMe2OH
EtX X
Me
CHC0
(iv) 2Et LiA1H4
>^^CHCÔH
Mn 2
° > (^^ CHC HO
Q. 20 The +I.E. ofthree methyl groups on central C-atom of tert-butyl alcohol makes is partially negative with
the result that it pushes the electron pair of -OH bond towards H-atom and thus H-atom is not replaced
easily.
CH3 h
^ - 5 + 0 I ' -6 +8
CH 3"^ C H CH3 -CH 2 -CH 2 -> C 0-«- H
t I
CH3 H
(less partial +ve charge) (more partial +ve charge)

Q.21 Oxygen atom in diethyl ether molecule has two lone pair ofelectrons available for co-ordination. Therefore
ethers behave as Lewis base forming oxonium salts.
r ^ > 0 : + HC1 > fÔH+Cl- (dialkyl oxonium chloride)
Q.22 Proof spirit is a technical term representing 57.1 % by volume ethanol-water mixture for the purpose of
tax lavied on its production. The percentage represents the weakest possible percentage which allows
the gun powder to catch fire.
Q. 23 Sodium metal reacts with ethanol to form sodium ethoxide ion because ofactive H atom in ethanol. Ether
do not have such active H and thus can be dried by sodium
1
C2H5OH + Na > C2H5ONa + - H 2
Q.24 Due to the formation of explosive peroxide by oxidation.
Q.25 Addition of methyl alcohol or naphtha or pyridine is made into ethyl alcohol to make sure that it will not
be used for bevarage purposes. This process is known as denaturation of alcohol.
^Bansal Classes Alcohols & Ethers [30J
Q.26 C2H5OH, C 2 H 5 HS0 4 , C 2 H 5 - 0-C 2 H 5
Q.27 Ethanol being very weak Lewis base and thus reacts with stronger acid HI
Q.28 (i) CH 3 CH 2COOH (ii) CH3COOCH2CH2CH3 (iii) MePhS0 2 0CH 2 CH 2 CH 3

O
-CH 2 CH 2 CH 3
(iv) PhCOOH + PhCOOCH 2CH2CH3 (v)
OH
Q.29 (A) \^J ( B ) ^ ( c)
CJ
(D) CH2 = CH-CH2(C1) - CH3 (E) CH3CH(C1)CH 2CH2CH0
(F) CH3-CH(C1) CH2CH 2CH2OH
CH?OH
Br
NFL
2
OMe
Q.30 (a)[Ol r (b) (c)Ph-CH(Cl)-CH2 OH
CH 2 Ph
Me' t) H OH
(d) H 3 C-CH 2 -C H 2 -C H 2 -S-CH 2 -(CH 2 ) 16 -C H 3
Q.31 (A) CH 2 =CH-CH2 -CH 2 OH (B) Bi-CH2CH(Br)CH2CH 2OH

Br CH 2 OH
CI—| H ( F ) Me-CH-CH 2
(C)
0 «Q Me O
Q. 3 2 (a) m-nitrophenyl acetate (better leaving group)(b) p-nitrophenyl acetate (better leaving group)
(c) sodium salt of phenol (better nucleophile) (d) sodium salt of phenol (better nucleophile)
(e) Phenol (more activated aromatic ring.)
+
Q.33 S n 2 attack on a carbon of a benzene ring does not occur nor does the high energy C 6 H5 form by an
SN1 reaction. Hence ARL cannot be a product even in an excess of conc. HI
Q.36 (a) (b) 0 < H
Ph
I
Q 37 Ph - C - CH3
I
Br
r
Q 38 V-Cli-,OH ^" / v
> - H 2 Q H
Q.39 (A) C2H5C1; (B) C 2HSCN; (C) C2H5COOH; (D) C2H5COONH4

(E) C2H5CONH2
Q.40 (A)C3H7Br; (B) CH3CH=CH, (C) CH3CHBrCH3 (D) CH3CHNH2CH3
EXER CISE-III
OH
Q.l A:— CH3 - CH - CPI3
H H H O
! I I I!
Q.2 (A) C - C - C - C = C (B) C - C - C - C - C (C) C - C - C - C - C
OH OH OH
OH Br OH O
Q3 (A) Ph - CH = CH - CH - CH 3 , (B) Ph - CH - CH - CH - CH 3 , (C) P h - C H = C H - C - O - H
Br
CH 2 CH3 0
1! I II
Q4 (A) C - C - C - C - C - C , (B) C H 3 - C H 2 - C - C H 2 - C H 2 - C H 3 , ( C ) C- C- C- C- C- C
OH
CH2 CH3
(D) Et - CH - CH 2 - CH = CH 2 , (E) Et - CH - CH 2 - CH2 - OH, (F) Et -CH-CH 2 - C 0 2 H
CH 3
CH, CH, CO C
I II I .11 I
(D) CH3 - CH - CH - CH 2 - CH 3 , (G) C - C - C - C - C , C- C- C- C- C-
OH
Q.6 C2H5OH C2H5C1

Ethyl alcohol Ethyl chloride
(X) (Y)
(!lBansal Classes Alcohols & Ethers [32]
Q.7 C H 3 - C H - C = C H2 CH3-CH-C-CH2OH
CH 3 C 2 H 5 CH 3 C 2 H 5
(DJ (E)
H
CH3-CH-C-COOH CH, - CH - C = O
CH 3 C 2 HJ CH 3 C 2 H 5
(F) (G)
Q.8 (CH 3 )2 CHOH; CH 3 COCH 3 ; CH 3 COOH; CHGCCHG
NOH
(A) (B) (C) (D)
Q.9 (CH 3 ) 2 CHCH 2 0H; (CH^C-CH^ (CH 3 ) 3 COH
(A) (B) (C)

Q.10 C 2 H 5 OC 2 H 5 ; C2 H 5 I; C 2 H 5 OH
(X) (Y) (Z)
Q. l l Four OH groups are present in compound A.

CH 2 OCOCH 3
CHOCOCH,
CH 2 CH CH CH 2
CHOCOCH,
OH OH OH OH
(A) CH 2 OCOCH 3
(B)
C2H5
Q. 12 C2H5
H X - C - C = CH
CH 3 —C—CH 2 — CH 3
OH
(A) OH
n(B)
Q.13 CH 3 H CH 3 — CH — CH 3 CH 3 — C — CH 3
7
Vc OH o
H / \ H (B) (C)
(A)
Q.14 CH 3 CH 2 CH 2 C(CH 3 ) 2 CH 3 CH 2 CH 2 C(CH 3 ) 2 CH 3 CH 2 CH 2 C(CH 3 ) 2

CI
OH ONa
(B) (C)
(A)
CH 3 CH 2 CH = C(CH 3 ) 2
(D)
Q.15 (A) CH 3 CH 2 CH 2 CH 2 0H (B) CH 3 CH 2 CH 2 CH 2 1

(C) CH 3 CH 2 CH 2 CHO (D) CH 3 CH 2 CH 2 COOH
Q. 16 (A) CH 3 CH 2 0H (B)CH 3 CHO
Q. 17 (X)C 2H 4C1 2 (Y)C1CH2CH 2C1 (Z)CH3 CHC12
Q.18 CH 2 CH 2 CH 2 C = CH
i
OH
(X)Pent 4-yn-l-ol
CH,
Q.19 (A) \CHOH (B) CH 3 -CH=CH 2 (C) CH .C .C H (D) CH 3 COCH 3
C H /
+1IBR
Q 20 CH 3 -CH 2 -CH=CH-CH 2 -CH 3 > CH 3 - CH 2 - CH 2 - CH - CH 2 - CH 3
Br
(A) (B)
CH 3 - CH 2 - CH 2 - CH - CH 2 - CH 3
OH
(C)
Q.21 (A) CH 2 =CH-CH(CH3 ) 2 (B) CH 3 - C H - H C ( C H 3 ) 2
Br
(C) CH 3 - C H C H ( C H 3 ) 2 (D) CH 3 CO CH(CH 3 ) 2

I
OH
OH
Q.22 (A)HO-C-C-C-C (B) C = C ' - C - C (C)C-C-C-C
[36]
faBansal Classes Alcohols & Ethers
EXERCISE-IV (A)
Q.l D Q.2 B Q.3 D Q.4 A Q.5 C

Q.6 D Q.7 B Q.8 A Q.9 C Q.10 B
Q.ll D Q. 12 B Q.13 D Q.14 B Q.15 C
Q.16 A
EXERCISE-IV (B)
Q. l n-butanol is oxidised 4
carbinol carbon atom. by KM n0 and not t-butanol as the latter does not contain H atom attached to
CHjCHjC HjCHjOH + KMn0 4 -—> CH,CH 2 CH 2 COO OK + Mn0 2 + KOH

n-Butanol Brown
CH 3
CH3-C-CH3 +KMn04 > No reaction
OH
t-Butanol
H Me H Me Me
j |
H+
-> C H 3 - C — C - C H 3 - H 2° > C H 3 - C H - C - C H 3
Q.2 CH3-C —C -C H 3 -
1 1
Me
:OH Me HIOH Me
1,2-methyl shift
Me Me
+
-H
C H 3 - C = C - C H 3 <- CH, - CH - C - CH,
J
i | +
Me Me
Q.3 (D) Ph - CH - CH 3 (E) C fi H,COOH
OH
Q. 4 The ether formation involves nucleophilic substitution of alkoxide ion for halide ion.
R'0~+R-X R'0~+R a Slow

->R' 0 R X - ^ R ' - O - R + X-
3° alkyl halide can also involve elimination of HX to give alkene in the presence of a base. So, it is better
to start with 3° alkoxide and 1° alkyl halide, i.e., equation (b)
Q.5
X Q.6 Due to intermolecular H-Bonding
Q.7 A = C H 3 - C - 0 H , B = C2H5018H
Br Br Me
MgBr BrMgOCHMe HOCHMe
Q.8 Mg MeCHO . H,0
(A) (B) (C)

Mechanism
H-,0 CHMe CHMe
HOCHMe
Br
^ y / M e Me
Br~
2°carbonium 3° carbonium
Q.9 X : CO, ; Y : CH , = C H - C O O H ; Z : CH,2 = CH CH -O

2
H ; CH,0 RCT+RQC
Ph H (+)CH3 CH 2-C-OH
CH3
Q.10 CH 3 - C - CO OH + C H 3 - C - COO H
conc. H,SOa , A
H Ph
(recemic mixture)
Ph H H H
CH, - C - C - O - C - CH 2 CH 3 + CH 3 - C - C - O - C - CH 2 C H 3
H O CH 3 Ph O CH ,
during esterification reacti on only - COO H and - OH participates. The re is no effec t on structure o f
configuration of carbon adja cent of these groups. S o when ( ±) acid reacts with pure (+) alcohol two
esters are produced whine are diastereoisomers of each other.
CH,
Q.ll P: C H 3 - C H 2 - 0 - C - C H 3
Q : CH 3 CH 2 OH
R : C H 3 - C - C H3
when ethylene reacts with dil. H 2 S0 4 CH 3 CH 2 ® is produced during rate determining step, whereas P
gives resonance stabilized intermediate.
CH, CH,
CH3-CH2-O-C-CH3 C H 3 ~ C H 2 -O = C~CH 3
due to extra stability of intermediate the rate of reaction is very fast
| BANSALCLASSES
TARGET IIT JEE 2007
ORGANIC CHEMISTRY
xni( XY Z)
AROMATIC
COMPOUNDS
C ONTENTS
EXERCISE-I
EXERCISE - II
EXRECISE-III
EXRECISE-IV(A)
EXRECISE-IV(B)
ANSWER KEY
EXERCISE-I
Q. 1 How many n electron are there in the following species:

©
(A) 2 (B) 4 (C) 6 (D)8
Q.2 Number of n electrons present in naphthalene is:

(A) 2 (B) 4 (C) 10 (D) 14
Q. 3 Which of the following is not the property of benzene:

(A) Characteristic smell (B) Inflammable
(C) Unsaturation (D) Colourless
Q. 4 Benzene undergoes substitution reaction more easily than addition because:

(A) It has a cyclic structure (B) It has three double bonds
(C) It has six hydrogen atoms (D) Of resonance
Q.5 The order of reactivity of following compounds:

(I) <j) - CI I, (II) f- CH 2 -CH 3 (III) <()-CH(CH3)2 (IV) <|>-C(CH3)3
towards electrophilic substitution will be-[where <j>=C6H5]
(A) I > II > III > IV (B) IV > III > II > I (C) II > I > III > IV (D) III > II > I > IV
Q. 6 Which one of the following is the most basic compound:

(A)C 6H5-NH 2 (B)C6H5-NHCH3 (C) C6H5-N(CH3)2 (D) C6H5N(C2H5)2
Q.7 Find odd compound out:

(A) Lindane (B)Gammexane (C) 666 (D)HCB
Q. 8 Which of the following reagents and conditions convert benzene to chloro-benzene:

(A) Cl2, sunlight, heat (B) HC1, heat (C) HC1, sunlight, heat (D) Cl2, A1C13, cold
Q. 9 Which order is correct for the decreasing reactivity to ring monobromination ofthe following compounds:
(I)C6H5CH 3 (II) C6H5COOH (III)C6H6 (IV) C6H5NO2
(A) I > II > III > IV (B) I > III > II > IV (C) II > III > IV > I (D) III > I > II > IV
Q.10 Benzene on treatment with a mixture ofconc. HN0 3 and conc.H2S0 4 at 90°C gives:
(A) Nitrobenzene (B) m-Dinitrobenzene (C) p-Dinitrobenzene (D) o-Dinitrobenzene
Q. ll Which of the following structures correspond to the product expected, when excess of C6H6 reacts with
CH2C12 in presence of anhydrous A1C13:
(B)Q-CHCL 2
€1
to Bansal Classes Aromatic Compounds Page # 2
Q. 12 For preparing monoalky! benzene, acylation process is preferred than direct alkylation because
(A) In alkylation, a poisonous gas is evolved
(B) In alkylation. large amount ofheat is evolved
(C ) In alkylation, pollyalkylated product is formed
(D) Alkylation is very costly
Q.13 Benzene reacts with n-propyl chloride in the presence of anhydrous A1CL to give predominantly:
(A) n-Propylbenzene (B) Isopropylbenzene
(C) 3-Propyl-1 -chlorobenzene (D) No reaction
Q.14 In the sulphonation. acetylation andformylationof benzene the group of effective electrophiles would be:
(A) SO:,CH 3 = O.H CO (B) SO3.CH3 -C = O-HCO

(C) SO v CH 3CHO, CO + HC1 (D) HS 0 3 , CH 3 CO, HCO
( Q. 15) Number of benzene derivatives of C7H7C1 is:

^ ^ (A) 2 (B)4 (C) 5 (D)6
Q.l 6 The number of benzene derivatives

(A) 2 (B) 3 of the formula C ?Hg O is:
(C)4 (D)5
Q.17 Ethyl benzene + Cl7 — ( m a i n ) compound is:

(A) o-& p-chloroethylbenzene (B) 1 -Chloroethylbenzene
(C) 2-Chloroethy 1 benzene (D) m-Chloroethylbenzene
Q.18 Chlorinaton of toluene in die presence oflight and heat followed by treatment with aqueous NaOI I gives:
(A) o-Cresol (B)p-Cresol
(C) 2,4-Dihydroxytoluene (D) Benzyl alcohol
Q.l 9 p-Nitrotoluene on further nitration gives:

CI-I3 CH 3 CH 9 OM
r r N ° 2 r S (C)V^ fr (D) ^
(A)1^ NO 2
NO-, NO, " NO , OoN
Q.20 In the reaction of p-chlorotoluene with KNH2 in liquid NH,, the major product is:
(A) o-Toluidine (B)m-Toluidine (C) p-Toluidine (D) p-Chloroanilinc
Q.21 Maj or product of this reaction will be:

CH,
AICI3.A
(A) o-xylene (B) p-xylcne (C) both (D) m-xylene
Q.22 C6H5CH3 C r 0 ^ >A >B

The functional group present in B and name ofthe reaction would be
(A) -CHO, Gattermann aldehyde synthesis (B) -CHO, Etard reaction
(C) -COCH3, Friedel Crafts reaction (D) -CHO, Oxo reaction
Q.23 Which chloroderivative of benzene among the following would undergo-hydrolysis most readily with
aq.NaOH to furnish the corresponding hydroxy derivative.
.N0 2
(A)02N-/oV-C1 (B)02N-<O)-C1
(
NO2
(C) Me2N CI (D)(oyC\
Q.24 . The order of relative reactivity of the given halides towards S N2 reaction is:
(A) PhCH2Cl > PhCHClCH3 > PhCCl(CH3)2
(B) PhCH Cl < PhCHCl(CH ) < PhCCl(CH )
2 3 3 2
(C)PhCHCl(CH 3 )>PhCH2 Cl>PhCCl(CH3 ) 2 .
(D) PhCHCl(CH3)>PhCCl(CH3)2 > PhCH2Cl
Q.25 An aromatic compound A' C7H6C12, gives AgCl on bonding with alcoholic AgN0 3 solution, and yields
C?H70C1 on treatment with sodium hydroxide. 'A' on oxidation gives a mono chlorobenzoic acid which
affords only one mononitro derivative. The compound A is:
CH,C1
CH 2CI CH 2CI
(A)^ (B)^C1 (C)[|rC1 (D)(OlCH2CI

Q.26 Which ofthe following reactions will not take place:
0 H
(A) ArN® + CuBr > ArBr (B) ArNf + PhOH > Ar ^ O V
(C) ArN® +H 3 H0 2 H2O >ArH (D ) A r N © + I - >Ari
Q.27 Which of the following substituted benzene derivatives would furnish three isomers in significant amount
when one more substituent is introduced:
CI Br
<A>fol wlSC <c>(ofBr <D>fo
Q.28 Which ofthe following reaction does not take place?

Br
knh
(A) CH3 OCH3 2 > (B) - ) - CI + aq. KOH -
liq.NH,
C1
300°C
300 L
(C) H - CI + ale. KOH > (D) If j + NaOH >
V ' 1 1' J 200 atm
Q.29 m-Bromotoluene is prepared by:
(A) Bromination of toluene
(B) Friedel Craft's reaction of bromobenzene with CH3C1
(C) Bromination of nitrobenzene and subsequent replacement of - N 0 2 group with methyl group
(D) Bromination of aceto-p-toluidine followed by hydrolysis and deamination
Q.30 Benzyne intermediate is not observed in:

OCH 3 CI CI +
(A) ( o f (B) (O [ £ )
OCH3
NaNH 2 >
Q.31 O ~~ A, maj or product A and reaction R are:
Br
OCH,
2
(A) I O I , elimination addition (B) j , elimination addition
l
2
OCH, OCH,
(C) O I , cine substitution (D) O .additionelimination
Q.32 Chloral+ {Q^ >- C1 Conc.H 2 SQ 4 ) product. The product is:

(A) Lindane (B) DDT (C)Tefflon (D) Ethaneperchlorate
Q.3 3 Which ofthe following group is divalent:
(A) Benzoyl (B) Benzyl (C)Benzal (D)p-Tolyl

a
Q.34 C6H6 + A 'C»3 > C6H.CONH2
A in the above reaction is:
(A) NH2CONH, (B) C1C0NH2 (C) CH3CONH2 (D)CH2(C1)C0NH 2
Q. 3 5 When benzene is heated with acetic anhydride in the presence of anhydrous aluminium chloride at 80°C,
the product formed is:
(A) Benzoic acid (B) Benzophenone (C)Acetophenone (D) Ethyl phenyl ketone
CH C0C1
Q.36 CJL 3
6 6
AlC lj HCl
The end product in the above sequence is:

(A) Toluene (B) Ethyl benzene (C) Both the above (D)None
Q.37 The species responsible for nitration and sulphonationby nitric acid conc. H2S0 4 andfirmingH2S0 4 are:
(A) N0 2 and S0 3 (B) NO+ and S0 3 (C) NO+ and S0 2 (D) N0 2 and S0 2
Q. 3 8 (A)
Which
C6Hof6the
+ +following
N0 2 •reactions
C6 H5 N0is2 not
+H an+ example
(B)of
Celectrophilic substitution:
A1C1
fiH5 + CH3C1 3 > C6 H 5 - CH3 + HCl
OH
uvlight
(C)C6H6 + Cl2 > C6H6C16 (D)C6H5OH + CO + HCl > K>)
AC3
Q.39 { ( J ) + CH2CH2CH2C1 ' ' > hydrocarbon (X) major product X is:
CH,
CH,
I
C
(A) < 0 ^ CH 2 CH-CH 3 (B) < O y ~CH
|
CH
(C) CH2CH2CH2CH3 . (D) None is correct
Q.40 Reaction ofS0 3 is easier in:

(A) Benzene (B) Toluene (C) Nitrobenzene (D) chlorobenzene
Q .41 Ifthe mixture of the following four aromatic compounds on oxidation by strong oxidising agent gives:
CH3 C2Hs C H 2 OH CHO
(A) Mixture of C6H5CH2OH + C6H5COOH (B) Mixture of C6H5CHO + C6H5COOH

(C) Only C6H5COOH (D) None of the above
Q.42 Methyl group attached to benzene can be oxidised to carboxyl group by reacting with:
(A)Fe 2 0, (B)AgN03 (C)KMn0 4 (D) Cr0 3
CH=CH2
Q.43 (O) ^ >B
Compound A and B respectively are:

(A) o-Bromostyrene, benzoic acid (B) p-Bromostyrene, benzaldehyde
(C)m-Bromostyrene, benzaldehyde (D) Styrene dibromide, benzoic acid
Q.44 Which of the following is the strongest o,p-directing group?
(A) OH (B) CI (C) Br (D) C6H5
Q .45 The reaction of benzene with CO and HCl in the presence of anhydrous A1C1, gives:
(A) Chlorobenzene (B) Toluene (C) Benzyl chloride (D) Benzaldehyde

Q.46 The number of benzyl ic hydrogen atoms in ethylbenzene is:
(A) 3 (B) 5 (C)2 (D)7
Q.47
ci
"X" —— 2 —V iRp.n?:ofrichioride Hydrolysis Y
)
X and Y respectively are:

(A) Benzene, Benzaldehyde (B) Toluene, Benzaldehyde
(C) Toluene, Benzoic acid (D) Benzene, Benzoic acid
Q. 4 8 Product obtained when benzoyl acetic acid is heated with soda-limeis:
coch b C00H
(a)<^0^- 3 ( )(o^ (0<0>CH3 (D)
Q.49 Etard reaction in the following is:
(A) Oxidation of toluene to benzaldehyde by chromylchloride
(B) Oxidation of toluene to benzaldehyde by alkaline KMn04
(C) Dry distillation of calcium benzoate
(D) Reaction of benzene with Cl2 in the presence of UV light
Q. 5 0 The highest yield of m-product is possible by the electrophilic substitution of the following:
(A)C 6H5 CH 3 (B) C6H5CH2COOC2H5
(C) C6H5CH(COOC2H5)2 (D) C6H5C(COOC2H5)3
Q-51 F OJ + H2 Ni, high temp, > (A). Which ofthe following can be isolated as the product ofthis reaction.
^ ^ high pressure
( A ) Q ( B ) 0 ( C ) 0 (
Q. 5 2 Which of the following is/are produced when a mixture of benzene vapour and oxygen is passed over
V 2 0 5 catalyst at 775 K?
(A) Oxalic acid (B)Glyoxal (C) Fumaric acid (D) Maleic anhydride
Q. 5 3 Which ofthe following is the least reactive in the case of bromination:

(D)Anisole
(A) Phenol (B) Aniline (C) Nitrobenzene
Q. 54 No. of 7t electrons in is:
O
(A) 2 (B)4 (C)5 (D)6
Q. 5 5 Which ofthe following is not an aromatic compound:
(A)
O (B) (C)
Q. 5 6 Benzene on reaction with A' forms j Q) which on reaction with 'B' forms I Q
'A' and 'B' are:
(A) Zn(Hg) + conc. HCl, Cl,LiAlH4

O
(C) "Cl,NaBH Cl,Zn(Hg) + conc. HCl
Q.57 In a reaction of C6H5Y, the major product (>60%) is m-isomer, so the group Y is:
(A)-COOH (B)-Cl (C) -O H (D)-NH 2
Q.5 8 Which ofthe following will undergo sulphonation at fastest rate ?
(A) (B) (Q
Q.59 Aniline under acidic medium, when chlorinated, produces:

(A) o-chloro aniline (B)m-chloro aniline
(C)p-chloro aniline (D) Mixture ofortho and para-chloro aniline
Q.60 Which ofthe following undergoes chlorination at fastest rate?
OH NH, NHCH3 NMe ,
(A) (B)| (C) (D)

lJ
Q. 61 Which of the following is most reactive towards sulphonation?
(A) m-Xylene (B)o-Xylene (C) Toluene (D) p-Xylene
Q. 62 Which ofthe following undergoes sulphonation at fastest rate ?

(A)C 6H 5NO 2 (B) C 6H5CH2NO2
(C) C6H5 CH 2 CH 2 N0 2 (D)|
Q.63 Which ofthe following undergoes nitration fast?
NH 2 N(CH 3 ) 3 C H 2 -NM e 3 CH 2 CH 2 NME 3
(A) [| 1 (B)f|^l (C)| (D)
Q. 64 When sulphonilic acid (p-H 2NC6H4S03H) is treated with excess of bromine, the product is:
(A) tribromo product (B) dibromo product
(C) monobromo product (D)tetrebromo product
Q. 6 5 Ring nitration ofdimethyl benzene results in the formation ofonly one nitro dimethyl benzene. The dimethyl
benzene is:
GH 3 CH,
(A) a s .*>(% (O i (D) None ofthese
Q.66 If p-methoxy toluene is nitrated, the major product is:
CH, CH, CH2N02

NO,
no
(A) (B) 2 (C)V^ (D) No reaction
OCH 3 OC H 3 OC H 3
Q.67 Ifmeta-nitroanilineis chlorinated, the maj or product is:

NH,
NH, NH, NH,
(A)^^-N02 (B) (C) (D) O

N O, -NO, NO,
CI
Q.68 An aromatic compound of molecular formula C gH4Br2 was nitrated when three isomers of formula
C6H3Br2N02 were obtained. The original compound is:
(A) o-dibromobenzene (B) m-dibromobenzene
(C) p-dibromobenzene (D) None of these
Q. 69 Which of the following carbocations is expected to be most stable?

CH, CH-, CH,
(A) |l (B) |MJ <c)(! m (D)

H'—Y H^Y
Q.70 Which of the following carbocations is expected to be most stable?

NO 2
(A) (B )(J (C) (D)|
Q. 71 (A)
The2number ofdisubstituted
.(B) 3products of benzene(C)4
is (D)5
Q. 72 Which of the following species is expected to have maximum enthalpy in an electrophilic aromatic
substitution reaction?
H®+ E
(I) (II) (HI) (IV) (V)
(A) Species (II) (B) Species (III) (C) Species (IV) (D) Species (V)
Q. 7 3 For the electrophilic substitution reaction involving nitration, which of the following sequence regarding
the rate of reaction is true?
-6 6> ^6n 6> ^r6 6

ll U l x ( B
) k
C6H6 < k
C6D6 < k
C6T6
k k k k k k
( Q CfiHfi = CfiD, = C,Tfi (D) C f i H f i >' CfiDfi < C,Tfi
Q. 74 For the electrophilic substitution reaction involving sulphonation, which ofthe following sequence regarding
the rate of reaction is true?
K K K k < k < k
(A) C FI H FI > C,D, > C,T, (B) C6H6 C 6 D 6 C 6 T 6
k k k
(D) CfiHfi > CfiD < C,Tfi
Q. 7 5 The order of relative reactivity of the given halides towards S N1 reaction is

(A) benzylchloride > p-methoxybenzylchloride > p-nitrobenzylchloride
(B) p-methoxybenzylchloride > benzylchloride > p-nitrobenzylchloride
(C) p-methoxybenzylchloride > p-nitrobenzylchloride > benzylchloride
(D) benzylchloride > p-nitrobenzylchloride > p-methoxybenzylchloride
EXERCISE -II
Q.l Which ofthe following will show aromatic character:
(a) (B> (c) (D)

00 0 0 l!)
Q.2 Which aromatic compound is obtained when n-octane undergoes catalytic hydroforming:
(A) ethyl benzene (B)m-Xylene (C)o-Xylene (D)p-Xylene
Q,3 Benzoic acid may be prepared by the oxidation of:
CH 2 CH 3 CH 2 OH COCH3 - OH
(A)[o] (B)[o] (Ofof < D )(Oj
Q.4 In which ofthe following reaction t-butylbenzene is formed:

Bp3 HF
(A) Benzene + iso-butyl chloride, A1C13 (B) Benzene + (CH3)2C = CH2 ' )
(C) Benzene + t-butyl alcohol h i so 4 > (D) Benzene + (CH3)2 C= CH2 Al c ' 3 >
NaOH H2, 0
Q.5 [OJ 395QC ' Product is:
(A)gf0H (B)@t0H W.J§f ^loT01

Q.6 Which ofthe following reactions of benzene proves the presence ofthree carbon-carbon double bonds
in it:
(A) Formation of a triozonide -
(B) Hydrogenation of benzene to cyclohexane
(C) Formation of C6H6C16 by addition of chlorine
(D) Formation of nitrobenzene on heating benzene with a mixture of concentratednitric acid and sulphuric
acid
Q.7 Electrophile NO® attacks the following in which cases NO® will be at metaposition:
CCI3 N02 NM e 3 Oe
• ^ ( 0 ) iQ(o)
Q. 8 Benzene is a resonance hybrid mainly oftwo Kekule structures. Hence:

(A) Half of the molecules correspond to one structure, and half of the second structure
(B) At low temperatures benzene can be separated into two structures
(C) Two structures make equal contribution to resonance hybrid
(D) An individual benzene molecule changes back and forth between two structures
Q. 9 The reaction of replacement of a hydrogen atom in benzene by alkyl group can be brought about with the
following reagents :
(A) Alkyl chloride and A1C1, (B) AlkeneandAlCl3
(C)Alkanol and alkali (D)Alkanol and acid
Q.10 Which of the following is /arefittingreaction:

(A) C6H5I + 2Na + ICH3 » C6 H 5 - CH 3
(B)C6 H 5 I + 2Na + IC6 H5 > C 6H 5 - C6 H5
(C) CH I + 2Na + ICH > CH, - CH
3 3 3
(D) C6 H 5 CH 2 -C1 + 2Na + C1CH2C6H5 -
Q.ll Which of the following statements is correct:
(A) Bromination of toluene occurs faster than that of benzene
(B) Nitration of toluene is faster than that of ethylbenzene
(C) The bromonium ion is a good nucleophile
(D) Effective nitrating agent is nitrate ion
Q. 12 Electrophilic substitution in cinnamic acid will take place at:

(A) Ortho-position (B) Para-position (C) Meta-position (D) On side chain
Q.13 Which of the following gives Friedel Crafts reaction?

NH, NO,
(A) (B) (Q (D)
Q.14 Which of the following can be used in Friedel Crafts reaction?

CI
(A) (B)CH2 =CH-C1 (C)CH,CH2 C1 (D)CH 2 C H - C H 2 -C1
Q.15 The good method for converting benzene into propyl benzene is:
(A) C6H 6 + CH3CH 2CH 2C1 + Anhyd. A1C13
(B) C6H6 + CH 3 CH 2COCI+Anhyd. A1C13 and then treatment with Zn/Hg/HCl
(C) C6H6 + CH3 CH 2 C0C1 + Anhyd. A1C13 and then treatment with H 2 Ni
(D)C6H6 + Anhyd. A1C13 + cyclopropane
Q.16 Which of the following will undergo nitration slow than benzene?
NH, CI N H CO CH ,
(D)
Q.17 Which ofthe following is ortho-para directing group?

(A) CF, (B) CC1, (C) -C H=C H- COO H ( D ) - N = C
Bansal Classes Aromatic Compounds Page #11
Q.18 Which ofthe following statements is true?

(A) Ortho-and para-directing groups increase electron density at ortho-and para-positions
(B) Meta-directing groups increase electron density at meta-position
(C) Meta-directing groups decrease electron density at meta-position
(D) Ortho-and para-directing groups decrease electron density at meta-position
Q. 19 Which ofthe following statements is/are not true?

(A) All ortho-para directing groups activates the ring
(B) All ortho-para directing groups except halogens activate the ring
(C) All meta-directing groups have rc-bond on the atom directly attached to the ring
(D) All meta directing groups are deactivating.
Q.20 Which ofthe following compounds can be classified as aromatic?

(A) 1,2,3-Triphenylcyclopropenium cation (B) Cyclooctatetraenyl dianion
(C)Azulene (D) 10-A^lene
Q.21 The structure ofthe compound that gives a tribromo derivative on treatment with bromine water is:
CH
' CH3 SO3H COOH
(B)[o 1 (C )(0 ) (D)[ oT OH

OH
Q.22 Amongst the following, the moderately activating group is

(A)—NHR (B)--NHC0CH 3 (C)—NR2 (D)—CH3
Q.23 False statement is / are :

(A) Although benzene contains three double bonds, normally it does not undergo addition reaction.
(B) m-chlorobromobenzene is an isomer ofm-bromochlorobenzene.
(C) In benzene, carbon uses all the three porbitals for hybridization.
(D) An electron donating substituted in benzene orients the incoming electrophilic group to the meta position.
Q.24
° ?
Of the species PhSH, PhSR, PhSR and Ph - S - OR the meta-substituted product is obtained from
H A I
y ?
(A)PhSR • (B) PhSR (C) PhSR (D) P h - S - O R
II H II
0 0 o
Q.25 Match the column:

Column A Column B
CH,
(A) FO I
+ CR 0
3
IN C H
3
C 0 0 H
• (P) Tropylium ion
(B) + Ph,C® >? (Q) Benzaldehyde
7> v
(C) [ O I + n-Pr Br + ZndL >? (R) Two types of products
CH 3
(S) Cumene
Q.26 Match the following:

Column I Column II
O-H
(A) C0 2 t is evolved from CP). O
NaHC03 by the reaction of

OH
(B) Libermann nitroso test is given by (Q)

NO 2
H-N-ME
(C) Compounds gives yellow oily (R)
liquid on reaction with NaN02 + HCl
(D) Compounds evolve a colourless gas (S) —N—(Ô^)
on reaction with active metals

Column I Column II
o o
n>\ 11 11
(A) Compounds which on reaction (P) Ph—C^TT ^C-
with neutral FeCl3 gives
violet / Blue colour are
(B) Compounds which on reaction (Q)
with Na0 3 S-^Q^)—N 2 C1
gives para red dye.
TMoTS] _
(C) Compounds which do not give (R) Ph-CH2-C-CH2CH3
yellow ppt. On reaction with NaOI
(D) Compound which have maximum % (S) q
of enol form

Column I Column II
(A) Compounds which gives Diels (P)

0
Elder's reaction in greater extent
withdienophile
(B) Compounds which undergoes (Q) O

ArSN reaction are
(C) Compound which has highest

« o
aromatic characters
(D) Strongest Base ..(S)

0
to Bansal Classes Aromatic Compounds Page #14
EXERCISE-III
Q. 1 Write the principal organic product in each ofthe following reactions:

CI
N 2
f^Y ° NO
HzNNH2
(i) L j l +C 6H5CH 2SK >A (ii) > B
| triethylene
CH, T GY
' COL
N02
CF, CI NH 2
(i)HN03.H2S04 ) D (iv) r^yS (l)NaN0^'HBr > E

V
(ii)NaOCH3 ,CH3OH (ii)CuBr
CI
r
(y) ® \ / OCH3 (i)NBS,Benzoyl peroxide,CC14,heat ^ p
3
V (ii)NaSCH,
CH,
JLNO 2 CI N 0 2
(vi) L j i +CH 3CH 2ONa >G (vii) f | T + C6H5CH2SNa >H
N02
NO 2
1 ^ heat
« O n - ^
Q. 2 Write the most stable resonance structure for the cyclohexadienyl anion formed by reaction of methoxide
ion with o-fluoronitrobenzene.
Q.3 Reaction of 1,2,3-tribrom-5-nitrobenzene with sodium ethoxide in ethanol gave a single product,
C8H?Br2N03, in quantitative yield. Suggest a reasonable structure for this compound.
Q.4 Offer an explanation for the observation that 4-chloropyridine is more reaction toward nucleophiles than
3-chloropyridine.
Q.5 2-Bromo-1,3 -dimethylbenzene is inert to nucleophilic aromatic substitution on treatment with sodium
amide in liquid ammonia. It is recovered unchanged even after extended contact with the reagent. Suggest
an explanation for this lack ofreactivity.
Q. 6 Two isomeric phenols are obtained in comparable amounts on hydrolysis of p-iodotoluene with 1 M
sodium hydroxide at 300°C. Suggest reasonable structures for these two products.
Q. 7 Given the structure ofthe cycloaddition product formed when benzyne is generated in the presence offuran.
^Bansal Classes Aromatic Compounds Page #15
Q.8 In each ofthe following reactions, an amine or a lithium amide derivative reacts with an aryl halide. Give
the structure of the expected product and specify the mechanism by which it is formed.
Br Br
Br X tjo
N
°2 H X H
Q.9 1,2,3,4,5-Pentalfluoro-6-nitrobenzene reacts readily with sodium methoxide in methanol at room

temperature to yield two major products, each having the molecular formula C 7H 3 F4 N0 3 . Suggest
reasonable structures for these two compounds.
Q.10 Suggest a reasonable mechanism for each ofthe following reactions:

(i)ExcessNaNH
(a) C.H.Br
6 3
+ CHL7(COOCHXH
1 3 )Z7 2>NH2 > CfiH5CH(COOCH2CH3)2
• ^ (ii)H20 °
CH 2 CH,CH,GH2 COCH 2 CH 3 (i)ExcessNaNH2,NH3 > ^ T r
(c)
a
L j J
C1
CH 3
NCH 2 CH 2 NHCH 3 NaNH2
ether
f ^ j
(ii)H20
CH 3
^
^
^ "
COOCH2 CH 3
CI CH3
F F
F x J ^ O C H 2 CH 2 OH F
T i] w > T iT J
(d)
heat
F F
tfe Bansal Classes Aromatic Compounds Page #16
EXERCISE - IV(A)
Q.l The cWorination oftoluene in presence offerric cUoride gives predominatly: [JEE 1986]
(A) Benzyl chloride (B) m-chlorotoluene (C) Benzal chloride (D)o-andp-chlorotoluene
Q. 2 Aiyl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halide due to
(A) The formation of less stable carbonium ion (B) Resonance stabilization
(C) Longer carbon-halogen bond (D) The inductive effect [JEE 1990]
Q.3 The most basic compound among the following is: [JEE 1990]
(A)Benzylamine (B) Aniline (C)Aeetaniline (D) p-nitro aniline
Q.4 Chlorination oftoluene in the presence of light and heat followed by treatment with aqueous NaOH
gives:
(A)o-cresol (B)p-cresol
(C) 2,4-dihydroxytoluene (D) Benzoic acid [JEE 1990]
Q.5 When nitrobenzene is treated with Br2 in presence of FeBr3 the major product formed is
m-bromonitrobenzene. Statements which are related obtain the m-isomer are: [JEE 1992]
(A) The electron density on meta carbon is more than on ortho and para position.
(B) The intermediate carbonium ion formed after initial attack of Br+ attack the meta position is least
(C)destabilized.
Loss of aromaticity when Br+ attacks at the ortho and para positions and not at meta position
(D) Easier loss of H+ to region aromaticity form the meta position thanfromortho and para position.
Q.6 Choose the correct statementfromthe ones given below for two aniline in: [JEE 1993]
+
NH 3 NH 3
(I) (II)
(A) II is not an acceptable canonical structure because carbonium ions are less stable than ammonium
ions .
(B) II is not an acceptable canonical structure because it is non aromatic
(C) II is not an acceptable canonical structure because the nitrogen has 10 valence electrons
(D) II is an acceptable canonical structure
Q.7 Most stable carbonium ion is: [JEE 1995]
+ +
( A) p- N02- C6H4- CH2 (B)C6H5 CH 2
(C) p - CI - C 6 H 4 - +CH2 +
( D) p- CH30 -C6H4 - CH2
Q. 8 Arrange in order of decreasing trend towards SE reactions: [JEE 1995]
(I) Chlorobenzene (II) Benzene (IH) Anilinium chloride (IV) Toluene
(A) II > I > III > IV (B) III > I > II > IV (C) IV > II > I > III . (D) I > II > III > IV
Q.9 Among the following statements on the nitration ofaromatic compounds, the false one is: [JEE 1997]
(A) The rate ofbenzene is almost the same as that ofhexadeuterobenzene
(B) The rate of nitration oftoluene is greater than that ofbenzene.
(C) The rate ofnitration ofbenzene is greater than that of hexadeuterobenzene
(D) Nitration is an electrophilic substitution reaction
Q.10 Nitrobenzene can be preparedfrombenzene by using a mixture of conc. HN0 3 and conc. H 2 S0 4 . In
the nitrating mixture HN0 3 acts as a: [JEE 1997]
(A) Base (B)Acid . (C) Reducing agent (D) Catalyst
Q.ll Benzyl chloride (C6H5CH2C1) can be preparedfromtoluene by chlorination with: [JEE 1998]
(A)S02Cl2hv (B)SOCl2 (C)Cl2hv (D)NaOCl
Q.12 The most unlikely representation of resonance structure of p-nitrophenoxide ion is: [JEE 1998]
w V / 0 -
w ° \ 5 /
(A)
O" O O" o
Q.13 A solution of (+) -2-chloro-2-phenylethane in toluene racemises slowly n the presence of small amount
of SbCl5, due to the formation of: [JEE 1999]
(A) Carbanion (B)Carbene (C) Free-radical (D) Carbocation
Q.14 Toluene, when treated with Br2/Fe,. gives p-bromotoluene as the major product, because the CH3 group:
(A) is para directing (B) is meta directing [JEE 1999]
(C) activates the ring by hyperconjugation (D) deactivates the ring
Q.15 Amongst the following the strongest base is: [JEE 2000]
(A) C6H5NH2 (B) p-0 2NC 6H4NH 2 (C) m-0 2NC 6H4NH 2 (D) C6H5CH2NH2
Q. 16 Identify the correct order ofreactivity in electrophilic substitution reactions ofthe following compounds :
CH, CI NO,
CO u J (II) ft n (III)[ r V (IV) II I [JEE 2002]
(A) I > II > III > IV (B) IV > III > II > I (C) II > I > III > IV (D) II > III > I > IV
(CH3)2NH ) ^ (i)NaNQ 2 HCl 0°~5 °C ^ ^
Q.17 F 2
[JEE 2003]
DMF (ii)H 2 Catalytic Reduction
H3CX
(A)02N-^0/-nh (B) N
H2CX H3 C
(C) (D) 1
h2C/
NH,
Q.18
Br
to Bansal Classes Aromatic Compounds Page #18
Q. 19 Which of the following is obtained when 4-Methylbenzenesulphonic acid is hydrolysed with excess of
sodium acetate? [JEE 2005]
C0
(A) °â (B ) CH
s- O + S0
3
(C) Ctt 3 SO3 N a + CHjCOOH (D) CH3 COCH3 + NaOH
EXERCISE - IV (B)
A1C1
Q.l [ O J + (CH3)2CH.CH2C1 3 >(A) [JEE 1992]
(i) Br,,Heat,Light
2 C H C >
Q- 6 5 2H5 (ii)NaCN [JEE 1994]
Q.3 An organic compound (A). CgH6 on treatment with dilute sulphuric acid containing mercuric sulphate
gives a compound (B), which can also be obtained from a reaction of benzene with an acid chloride in
the presence of anhydrous aluminium chloride. The compound (B), when treated with iodine in aqueous
KOH, yields (C) and a yellow compound (D). Identify (A), (B), (C) and (D) with justification. Show
how (B) is formed from (A) ? [JEE 1994]
Q. 4 Toluene reacts with bromine in the presence of light to give benzyl bromine while in presence of FeBr3 it
gives p-bromotoluene. Give explanation for the above observations. [JEE 1996]
Q.5 Show the steps to carry out the following transformations: [JEE 1998]
(a) Ethylbenzene > benzene
j? (b) Ethylbenzene > 2-phenylpropionic acid
Q.6 C6H5CH2CHC1C6H5 alcoholicKOH.heat ) ( A) + (B) [JEE 1998]
Q.7 C 6 H 5 CH - C H 2 (A ) ('>Na NH 2(3-0 EQUIV)^ ( B) [ J EE 1 9 9 8 ]

(ii)CH 3 I
Q. 8 Normally, benzene gives electrophilic substitution reaction rather than thus electrophilic addition reaction
although it has double bonds. [JEE 2000]
Q.9 , How would you synthesis 4 methoxyphenol from bromobenzene in NOT more than five steps? State
clearly the reagents used in each step and show the structures of the intermediate compounds in your
synthetic scheme. [JEE 2001]
Q.10Carry out following conversions in 3 or less steps.

COOH COOH
f o l > f o l [JEE 2003]
Q. ll A compound C9H702C1 exists in keto form A and enolic form B. Enolic form B predominates at
equilibrium. On oxidation with KMn0 4 1 gives m-chlorobenzoic acid gives structures ofA and B.
[JEE 2003]
Q. 12 7-bromo-l, 3,5-cycloheptatriene is ionic compound, whereas 5-bromo-l,3-cyclopentadiene can't ionise
even n the presence of Ag®, Explain why? [JEE 2004]
Q.13 Give reasons: [JEE 2005]
H,C
-Br
(a) (i)|j T \ : I I j c2HsOH(ag.) > acidic solution
ch
3
(ii) B r - { j K __ C2HsOH(aq.) ) neutral
CH,
(b) (i)02N^S^ NaOH(aq.) > p (liberated)

CH,
(ii) H3C NaOH(aq.) ) p is not libe rated

CH2N02
.0 -O
N
N 0
Conc.HNO
/^/ 2 r
(C) (i)
Conc"• H 2 SO 4 ^
NO 2
is formed but not
f Brown fumes and^)„ . NaBr + MnQ 1 _ A Con,HNo 3 ) C ( i n t e r m e d i a t e ) ffi , D(Explosive product)

Q- 14 [^pungentsmell J B *"
Find A, B, C and D. Also write equationsAto B and Ato C. [JEE 2005]
ANSWER KEY
EXERCISE -1
Q.l C Q.2 C Q.3 C Q.4 D Q.5 A Q.6 D Q.7 D
Q.8 D Q.9 B Q.10 B Q.ll D Q.12 C Q.13 B Q.14 B
Q.15 B Q.16 D Q.17 B Q.18 D Q.19 A Q.20 B Q.21 D
Q.22 B Q.23 A Q.24 A Q.25 A Q.26 B Q.27 C Q.28 A
Q.29 D Q.30 B Q.31 A Q.32 B Q.3 3 C Q.34 B Q 35 C
Q.36 B Q.37 B Q.38 C Q.39 D Q.40 B Q.41 C Q.42 C
Q.43 D Q.44 A Q.45 D Q.46 C Q.47 C Q.48 A Q.49 A
Q.50 D Q.51 A Q.52 D Q.53 C Q.54 D Q.55 B Q.56 D
Q.57 A Q.58 B Q.59 B Q.60 D Q.61 A Q.62 D Q.63 A
Q.64 A Q.65 C Q.66 B Q.67 B Q.6 8 B Q.69 B Q.70 D
Q.71 B Q.72 A Q.73 C Q.74 A Q.75 B
EXERCISE- II
Q.l A,B,D Q.2 A,C Q.3 A,B Q.4 A,B,C,D
Q.5 A,B Q.6 A,B,C Q.7 A,B,C Q.8 C
Q.9 A,B,D Q.10 B Q. ll A,B Q.12 A,B
Q.13 A Q.14 C,D Q.15 B,D Q.16 C
Q.17 C Q.18 A. Q.19 A,B,C Q.20 A,B,C
Q.21 B,C,D Q.22 B Q.23 B,C,D Q.24 C,D
Q.25 (A) Q, (B) P, (C) R, S, (D) R Q.26 (A) Q, (B) P,R,S, (C) R,S, (D) P,Q,R,S
Q.27 (A) P,Q,R,S, (B) Q, (C) P,Q,R,S, (D) p Q.28 (A) R, (B) S, R, (C) P, (D) S
EXERCISE-III
C6 H5 CH?S H,NNH CI Br
NO,
Q.l (i) (ii) (iii)
0,N
NO 2 OCH,
OCH 2 CH 3 SCH2 C6 H5
.N O 2 NO ,
(V) (vi) (viii)

CH,SCH, N' OCH3
NO,
OCH 2 CH 3
F 0CH 3/ 0~ Br J \ .Br
Q.2 Q.3
NO ,
Q.4 Nitrogen bears a portion of the negative charge in the anionic intermediate formed in the nucleophilic
addition step in 4-chloropyridine, but not in 3-chloropyridine.
Y ci
11 11 is more stable and formed faster than
(fe Bansal Classes Aromatic Compounds Page #21
Q.5 A benzene intermediate is impossible because neither on the carbons ortho to the intended leaving group
bears a prot on.
Q.6 3 -Methylphenol and 4-methylphenol (m-cresol and p-cresol). Q.7 I no
EXERCISE - IV(A)
Q. l D Q.2 B Q.3 A Q.4 D Q.5 A,B Q.6 C Q.7 D
Q.8 C Q.9 C Q.10 A Q . ll A,C Q.12 C Q.13 D Q.14 A,C
Q.15 D Q.16 C Q.17 B Q.18 D Q.19 C
EXERCISE - IV (B)
C(CH3)3
Q .l [ O
CH7CH CHBrCH, CHCNCH,

Br?
Q-2 f O A,hy "MO NaCN
1
o^
2-phenylpropane niitrile
C=CH COCH, COOK
Q.3 (A)[0 (B)(0) (C)(0)

Q.4 In presence of FeBr 3, Br 2produc es Br+(an electrophile) which attacks the benzene ring at o-,p-position
to give p-bromotoluene. In presence of light, side chain is attacked to produce benzyl bromide .
H-,0
Q.5 (a) (i) C 6 H 5 C H ( O H ) C = C H C 6 H 5 C H - C = C H -
-H-,0
OHJ
C 6 H 5 CH=CHCHO =^C6H5CH=C=CH C 6 H 5 CH=C=CH
OH
CFIH, COOH
Sodalime
(b) (i) f o l fO] > [O
CN COOH
CHOCH CHXCH CHCH3 CHCH3
KCN
(")fO hv fo] - ^ [ o
K0H (ALC)
Q.6 C 6 H 5 CH 2 CH 2 CHC1C 6 H 5 A > C 6 H 5 CH= CHC 6 H 5
(Cis and trans forms)
CH=CH, •,CHBrCH2Br C=CNa
Br-, NaNH2 3 eq. [ Q
Q.7 [ O -> f O
CH,I
C=C-CH,
Q.8 Benzene has resonance stabilization due to delocalisationof Tc-electrons. Also during electrophilic addition
reactions, it loses its aromaticity. In electrophilic substitution reaction aromaticity is retained.
Br ONa OMe OMe
Na OH conc. H 0 SO Na OH
Q.9 [ O AhighPr essure
SO.H
OMe
OMe
H,0
ONa
OH
Alternative rout
Br Br Br OMe
Br
Na0H
conc.H-SO,,
->IQ JO Me2S04
»i O
^ ^
] Na0H
)[o
A high Pressur e
1 H,cr
SO.H ONa OMe ONa
OMe
OH
COOH COOH COOH

conc.H 1 SO /1 H B F . /K H E ,
Q.10 (O) •
SO.H
* o
OH
0
C-CH 2 -CHO C=CH-CHO
Q.ll ^
(A) . . ( B ) .
Keto Enol
Enol form is more stable due to extended conjugation
O
n
C-OH
KMnO„
(A)
o CI
Q.12 On ionization 7-bromo-1,3,4-cycloheptatriene gives tropolium ion which is aromatic with 671 electrons.
Br
(©) + Br
5-bromo-1,3-cyclopentadiene can't ionise as it will in that case give highly unstable antiaromatic cation
with 4 71 electrons.
Br
-X- + Br
CH3
I
Q.13 (a) (i) H5C6 - C - OC2H5 + HBr(acid); (ii) no reaction due to partial double bond character
I-
CH
3
(b) (i)
j CT
CH 3
+ F - is liberated; (ii) Bimomecular mechanism is not possible in (ii) case
(c) (i) due to presence of lone pair of nitrogen atom NO group is electron denating and ortho, para
directing
(ii) N0 2 group is electron withdrawing and meta directing
(d) Due to reduction of central ring, three four membered antiaromatic rings become stable while on
recuction of terminal ring only one antiaromatic ring can be stabilized.
CH 3
Q.14. (A) H2S0 4, (B) Br2, (C) NO? , (D) t^J

NO ,
I BANSALCLASSES
^ TARGET IIT JEE 2007
ORGANIC CHEMISTRY
XII (ALL)
CARBONYL COMPOUND
CO NT EN TS
EXERCISE 1(A)
EXERCISE 1(B)
EXERCISE II
EXER CI SE III
EXERCISE IV (A)
EXER CISEIV (B)
ANSWER KEY
EXERC1SE-UA)
Q. 1 Gem dihalide on hydrolysis gives:
(A) Vic did (B) Gem diol
(C) Carbonyl compound (D) Carboxylic acid
Q.2 In the given reaction:
OH OH
C H 3 - CIH — CI - C H 3 _
(a) + (b)
I
CH3
(a) and (b) respectively be:
(A) CH3CHO and CH3CHO (B) CH3COCH3 and CH3CHO
(C) CH3COCH3 and CH3COCH3 (D) CH3COOH and CH3COCH3
Q.3 Acetophenone can be obtained by the distillation of:

(A) (C6H5COO)2Ca (B) (CH3COO)2Ca
(C) (C6H5COO)2Ca and (CH3COO)2Ca (D) (C6H5COO)2Ca and (HCOO)2Ca

Q. 4 Arrange these compounds in decreasing order of reactivity for the nucleophilic addition reaction:
(I) Acid chloride (II) Aldehyde (III) Ketone (IV) Ester
Select the correct answer from the codes given below:
(A) I > II > III > IV (B) IV > III > II > I ( C) I I I >I I > I >I V (D) I > IV > II > III
Q.5 Acetalorketalis:
(A) Vic dialkoxy compound (B ) a, o-dialkoxy compound
(C) a-alkoxy alcohol (D) Gem dialkoxy compound
Q.6 In the given reaction

O
(i)LiA1H
C Hd3 - CH 2? - C- CH 2 COOC
2
7Hs W >(A) 4 )
( i i ) H2 0/H®
[X] will be:
CH 2 -OH
(A) HCHO (B)IH + H«
CH 2 -OH
C +
< 4H,-OH OH (D)HCN
fa Bansal Classes Carbonyl Compound [21]


C6H5-C-H NH2OH/H®
[X]
II
O
[X] will be:
(A) Only syn oxime (B) Only anti oxime
(C) mixture of syn and anti oxime (D) secondary amide
Q.8 Schiffs base is prepared from:

(A) Carbonyl compound and primary amine (B) Carbonyl compound and secondary amine
(C) Carbonyl compound and tertiary amine (D) All of these
Q.9 Schiffs reagent is used for the differentiation between:
(A) HCHO and CH3CHO
(B) CH3COCH3 and CH3CHO
O o
II II
(C) C6H5 - CH2 - C - CH3 and CfiH5 - C - CH2 - CH3
(D) HCHO and C6H5CHO

Q.10 In the reaction sequence, [X] is ketone:
CH,
oh/a
[X] —k^4Z > HOOC - (OL ,)^ CH - COOH
[X] will be:
O O 0 0
(A)[ 1 (B)[ | (C)^ Y 3 (D)" 3 '
Q.ll Which one ofthe following compounds will give dimethyl glyoxal with Se02:
(A) Acetone (B) Acetophenone (C) Ethyl methyl ketone (D) Propanaldehyde
Q .12 In the given reaction

O
C H 3
(^J -J5°a-> [X]
[X] will be:
O
9 ft 9
" U
Q.13 Consider the given reaction:
O O
c h c o o o h
C H 3 - C - CH 3 6 5 > C H 3 - C - O - C H 3
The above reaction is known as :

(A) Baeyer-villiger oxidation (B) Oppenaur oxidation
(C) Periodate oxidation (D) Peroxide oxidation

Q.14 Acetone can be converted into pinacol by :

(A)Mg/Hg/H,0 (B) Zn/Hg/HCl (C) N a / H g / H ^ (D) All of these
Q.15 Arrange acidity of given four compounds in decreasing order:
(I) CH3 - C - CH2 - C - CH3 (II) CH3 - C - CH3 (III) CH=CH (IV) CH,-CHO
Select correct answer from the codes given below:
Codes:
(A) I > IV> III > II (B) I > IV >11 >111 (C) III > I > IV > II (D) II > IV > I > III
OH
NaOH
x +Y - > CH3 - CH - CH - CHO
5°C " |
CH3
(X) and (Y) will respectively be:

(A) CH3-CH 2-CHO and CH3-CH 2-CHO (B) CH3-CHO and CH3 -CH 2 -CHO
CH 3
(C) CH3-CHO and CH r CHO (D) CH3-CHO and CH3 - C - CHO
CH,
Q.17 Number of products in the given reaction:
OH
C6HsCHO + CH3-CHO > Product
will be
(A) One (B) Three (C)Two (D)Four
Q.18 In the reaction:
5h /a
/\ _~_ yy 0 + wr " w > [X]
[X] will be
OH O OH OH O
OH
O
(A)f i f i (B)[ n i (c ) [ n i ( D ) ( ^
Q.19 Product ofPerkin reaction is:

(A) a, P-unsaturated aldehyde (B) (3-cyclohexyl a, {3-unsaturated aldehyde
(C) P-Aryl-a, {3-unsaturated acid (D) All of these
ISJ
(!§Bansal Classes Carbonyl Compound
Q 20 The product of the reaction:
N 0 2 - < 0 } - C H O + (C 6 H 5 -C H 2 C0 ) 2 0
|C 6 H 5 -C H 2 COONa/A
[X]
will be:
(A) C 6 H 5 -CH =CH-COOH (B) N O 2 - < o ) - C H = C H - C O O H
(C) C 6 H 5 -CH=C-COOH (D) N 0 2 - { o ) - CH = C - G OO H
c6H5
*no2

OH
QHXHO + X > C 6 H 5 - CH - CH 2 - COOC 2 H 5

6 5 6 5 2 2 5
(ii)HOH/NH4Ci
[X] will be:

(A) CH 3 -COOC 2H 5 (B) CH 3 -C H 2 -COOC 2 H 5
Brx
(C) BrXH 2 -COOC 2 H 5 (D) b^CH-COOC2H5
Q.22 The given reaction
C6fi H5s -CHO + Br-CH29-COOC22 Hc5 — ^

(ii)HOH/NH
>C 5 H,-CH=CH-COOC2
6 fi 2H5 5
4Cl
(iii)A
is known as:
(A) Perkin reaction (B) Knoevenagel reaction
(C) Reformatsky reaction (D) Claisen-Schmidt reaction
Q.23 Cannizzaro reaction is example o f:

(A) Redox reaction (B) Disproportionation (C) Both (A) and (B) (D) Only oxidation
CH 2 OH
Q. 24 Acetaldehyde can be converted into HO CH 2 - C - CH 2 OH by which reagent?
CH 2 OH
(A) KOH (B) KOH followed by LAH

(C) excess of HCHO and KOH (D) KCN followed by SBH
Q.25 Metaformaldehyde is:

(A) Dimmer of HCHO
(B) Trimer of formaldehyde
(C) Tetramer of formaldehyde
(D) Polymer in which number of HCHO unit is more than 100
(!§Bansal Classes Carbonyl Compound ISJ


O
CH , - C - CH 3 [ X]
Distillation
[X] will be:
(A) Methyl oxide (B) Phorone
(C) 1,3, 5-Trimethylbenzene (D) 2-Butyne
Q.27 Which will give silver mirror test with Tollens reagent:
(A)C6H5CHO (B)CH 3 -CHO (C) HCOOH (D) All of these
Q.28 Which one ofthe combinations will give propanaldehyde on dry distillation?
(A) (C6H5COO)2Ca and (HCOO)2Ca (B) (CH3COO)2Ca and (CH3CH2-COO)2Ca
(C) (CH3-CH 2-COO)2Ca and (HCOO)2Ca (D) (CH3COO)2Ca and (CH3COO)2Ca
Q.29 Grignard reagents do not give carbonyl compounds with:

(A) C0 2 (B) RCOC1 (C) RC-N (D)RCOOR
Q.30 In the reaction sequence:
Cyclohexane __hv/ci2 > (X) aio.KOH/A >(Y) (Z)
(Z) will be:

(A)Hexanal (B) 2-Hexanone (C) 3-Hexanone (D) Hexanedial
OH O
Aluminium tertiary butoxide ^
j) Acetone
is knows as:
(A) Kolbe reaction (B) Tischenko reaction (C) MPV reaction (D) Oppeneur oxidation
Q. 3 2 In the given reaction:
CO BH 3 0
t i i ) H 2 0 2 /0H
(Y)
(X) and (Y) are :
ISJ
Q. 41 Questions given below consist oftwo statements each printed as Assertion (A) and Reason (R); while
answering these questions you are required to choose any one of the following four responses:
(A) ifboth (A) and (R) are true and (R) is the correct explanation of (A)
(B) ifboth (A) and (R) are true but (R) is not correct explanation of(A)
(C) if (A) is true but (R) is false
(D) if (A) is false and (R) is true
Assertion: Benzaldehyde with HCN gives two isomeric compounds
Reason: Both nitrile and isonitrile compounds are possible when HCN reacts with carbonyl group.
Q. 42 When D-glucose is treated with Br, water then the product is:
C02H C02H OH CO 2 H
OH —OH —OH
HO -
HO- —OH
HO— HO—
—OH OH —OH
(A) (B) —OH (Q (D)
—OH — OH —OH — OH
—OH OH OH
CO?H
OH
Q.43 [(CH^CQ] 3 A1 A
A is:
OH
(A) (B)
(Q (D)
a
CH=CH-CHO
LlA1H4
) p r o d u c t is (B) ||^j-CH=CHCH 2 O H
(A) |^^|-CH 2 CH 2 CHO

(C) CHLJC^CHJOH (D) j^^CH 2 C H 2 C H 2 O H

Question No. 45 to 49 (5 questions)
Compound 'C fCF , - C - C ( C H 3 ) 3 1 was prepared in a three step sequence fr om ethyl trifluoroacetate.
I ^
[ 0 J
The first step in a sequence involved treating ethyl trifluoroacetate with NH 3 t o give a compound A. A on
treatment with reagent 'X' (alongwith gentle heating) produces a compou nd B (which on hydrolysis can
pr od uc e an acid). B on tr ea tm en t wit h an ora ng o metallic, 'Y', fo ll ow ed by h yydrolysis pr od uc es C.
Based on above passing att empt the following questions:
Q.45 Structutre o f 'A would be

0 O
J!
c
IIc
(A) ÔCH2CH? (B)H 2 N-^ ^ C F 3
CF 3 ^ c ÔCH 2 CH 3
(C) CF^ÔCH.CH, I!
NH, NH
Q 46 Structure of B would be
O
(A) CF, - C - NH 2 (B) CF 3 -C =N (C) CF 3 - C H 2 -C N (D) CF 3 -C H 2 - NH 2
Q.4 7 'X' should be

(A) Ba 0 2 (B)H202 (C)P4O10 (D)N20
Q. 48 When 'C is trea ted with perb enzo ic acid it will pro duc e
O 0
(A) CF3 - C - O - C(CH 3 ) 3 (B) (C H 3 ) 3 C - C - OCF 3
(C) CF3 - C - OH (D) (C H 3 ) 3 C-OH
O
rSH
-SH
Q.49 C— — » E : 'E' is
RaneyNi
CF3 H CF3 S
\C / \ / n
(A) / \ (B) / X ,
S
(CH3)3C OH (CH 3 ) 3 C
CF3 H O
\ /
c
I
(C) / \ (D)CF3 -C-S -C(CH 3 )3
(CH3) 3C H
<!%Bansal Classes Carbonyl Compound [9]

faiBansal Classes Carbonyl Compound [10]

EXERCISE-KB)
Q 1 Which one of the following is mixed ketone:
?
(A) C H 3 - C - C H 3 (B)CH3-CH2-C-CH3
s
o O
II - CH 3
(C) Ph - C • (D) CH3 - C 6 H 4 - C
II - CH 2 Ph
(P)
Q.2 In which of the following reactions product will be aldehyde?
(A) CH 3 - CH = C H - C2H5 - i i ) 0
3 > (B) CH 3 -CH=CH 2 CO/H2/CO2(CO)S__>
(II)H,0
CH 3 CH,
( C) C H 3 - C = C H - M ^ (D) C H3 - C .C H
NaOH,H202
Q. 3 Which one of the following alcohols can be oxidised by K 2 Cr 0 4 ?

(A) Ethanol (B) Tert butyl alcohol (C) Isopropyl alcohol (D)Allyl alcohol
Q.4 Two isomeric ketones, 3 -pentanone and 2-pentanone can be distinguished by :

(A) I,/ NaO H (B)NaS0 3 H (C) NaCN / HCl (D) 2,4-DNP
Q. 5 Consider the structure of given alcohol:
OH
C g H 5 - C • - CH3
C2H5
This alcohol can be prepared from:
° 11
(A) C 6 H 5 - C - CH 3 and C2 H5 MgBr (B) CH 3 - CH 2 - C - CH, and C 6H 5MgBr
O O
(C) C 6 H 5 C-
II C 2 H 5 andCH 3 Mg Br (D) C 6 H 5 -C-Cl
II and C 2 H 5 MgCl
Q 6 Stability ofhvdrates of carbonyl compounds depends on:

(A) Steric hindrance (B) Presence of - I group on gemdiol carbon
(C) Intramolecular hydrogen bonding (D) angle strain in carbonyl compound
(!§Bansal Classes Carbonyl Compound ISJ


C6H5 - C - CH3 NH2OH/Ha > pq [Y]
A
II
o
[Y] will be:
O O
II II
(A) C 6 H 5 -C -NHC H 3 (B) C H 3 - C - N H - C 6 H 5
0
(C) C6H5 - CH2 - C - NH2 (D) C6H5CH2CN
Q.8 Fehling solution gives red precipitate with:

(A) Aromatic aldehyde (B) Aliphatic aldehyde
(C) Ketones (D) a-hydroxy ketones
Q.9 Silver mirror test with Tollens reagent is given by:

(A) C6H5CHO (B) Ph-NH-OH
(C) C6H5 - CH2 - C - CH2OH (D) CH3CO
0
Q.10 Which one ofthe following compounds will not give aldol:
(A)Acetaldehyde (B) Formaldehyde
(C) Pivaldehyde (D) Crotonaldehyde
Q. 11 Knoevengcl reaction is catalysed by :

(A)NaOH (B)NH3 (C)EtOk (D) Pyridine
Q. 12 Cross Cannizzaro reaction is an example of:

(A) Redox reaction (B) Disproportionation (C) Isomerization (D) Dimerization
Q. 13 Which one of the following reagent(s) is/are used for the conversion ofketone into hydrocarbons?
(A)LAH (B)N2H4/H 202
(C) Mg Hg FÔ (D) NaHgHCl
Q. 14 Schiffs reagent gives pink colour with:

(A)Acetaldehyde (B) Formic acid (C) Acetic acid (D) Methyl acetate
Q. 15 Which ofthe following compound will give positive Tollens test
(A)CH3CHO (B)Ql 0 I 1
OCH 3
(C) CH3CH2CH2CH2CH --OCH
OCH3 (D)CH
(D) CH33-CH
-CH
ÔCH,
OH

In above reaction (A) and (B) will respectively be
(A) ci & CH3CHO (B) CH3CH2C1 &
(C) 0 < C H 3 & HCHO (D) c i X ^ X X ^ . & CH3CHO
Q.17 Which of the following for m stable hemiketal

O 0
II II
(A) Ph - C - Ph (B) HO - ( CH 2 ) 3 - C - CH 3
O
II O
II
(C) CH 2 OH - C - (CHOH) 3 - CH 2 - OH (D) HO - CH 2 - (CH 2 ) 4 - C - CH 3
Q.1 8 Which of the following is example of 1,4-addition reaction
O
II (i)NaCN
U)
(A)
V 1
CH^z = CH - C - H >
(ii)H 2 0
(B) CH Z, = C H - C - H —
H 2 O/H®
(C)|> + CH2(COOMe)2 ~ >

o
o o
U-CH-CN
CH CH CN
(D) I ' ^ -
Base • 6 r
Q. 19 Which of the following can be used for protection of carbonyl group
(A) CH 2 - O H - CH 2 OH / H®
(B) C H 2 - 0 H - C H 2 - C H 2 OH / H®
(C) HS-(CH 2 ) 3 -SH
(D) CH 2 0 H - C H 2 -CH0
Q.20 Mixture of Ph -C HO & HCHO is treated with NaOH t hen Cannizzaro reaction involves:
(A) Oxidation of HC HO (B) Reduction of HC HO
(C) Oxidation of Ph -C HO (D) Reduction of Ph -C HO
Q.21 Acetone give addition elimination reaction with

(A) Hydrotyl amine (B) Sodiumbisulphite (C) Hydrogen sulphide (D) Ylide
faBansal Classes Carbonyl Compound [13]

Q. 22 Which ofthe following will be soluble in sodium bicarbonate solution?

OH COQH OH SOjH
(a) u O
m (c)u cd)
Q. 23 Asparmate, an artificial sweetener is a peptide and has the following structure. Which of the following is
correct about the molecule?
h 2 N^
°7A
^^NNH
CH,
(A) It has four functional groups

(B) It has three functional groups
(C) on hydrolysis it produces only one amino acid
(D) on hydrolysis it produces a mixture of amino acids
Q. 24 Match List-I with List-II and select the correct answer using the codes given below the lists.
List-I (Compound) List-II (Used as)
O
II
(A) 1,4 addition (P) P h - C H 2 - C - C H = CH2
(B) Tautomerism (Q) PCC
O
(C) Allylic bromination (R)
(D) Preparation of Ketonefrom2° alcohol (S) NBS
Q. 25 Match list-1 with list-11 and select the correct answer using the codes give below the lists:
List-I List-II
Ka B 4
(A) CH 2 CH-CHO - " > (P) Acetal
(B) C6H5CHO + Ph-NH 2 ——-> (Q) Setoffs base
(C) C6H5COCH 3+CH 3-CH 2-NH 2 — i t - * (R) Unsaturated alcohol
(D) RCHO + 2RCFLOH —i^—> (S) Enamine
ISJ
Q. 26 Match list-I with list-II and select the correct answer using the codes give below the lists:
List-I List-II
0H
(A) C 6 H 5 CHO + HCHO > C 6 H 5 CH 2 OH + HCO O (P) Cannizzaroreaction
ANHY ALC 3
(B) C 6 H 5 -H+CH 3 COCI - ' > C 6 H 5 -CO-CH 3 (Q) Friedel Crafts reaction
ANHY ZNC 2
(C) C 6 H 6 +CO+HCI ' > C 6 H55 -CHQ (R) Reimer-Tiemann reaction
Cu.,CL
OH OH
(i)CHC 3/Alc K0H/A CH0
(O) ' - )[qJ" (S)Gattermann-koch aldehyde synthesis
ISJ
Q. 3 (b) Equilibrium constants for the dissociation (Kdiss) of cyanohydrins according to the equation
OH O
RCR'
I Kdiss II
RCR' + HCN
I
CN
Cyanohydrin Aldehyde Hydrogen
or ketone cyanide
have been measured for a number of cyanohydrins. Which cyanohydrin in each ofthe following pairs has
the greater dissociation constant ?
OH OH
I I
(i) CH3CH2CHCN or (CH 3) 2CCN
H
,C HCCHCN
,
M OH Cfi6H<CCN
5 ?
<
(ii) FI
CH,
Q. 4 Some Grignard reagents react with ethyl orthoformate, followed by acidic hydrolysis, to give aldehydes.
Propose mechanisms for the two steps in this synthesis.
O-CH 2 CH 3 O-CH 2 CH 3 0
H- C- 0 - CH2 CH3 +R -M g- X >R-C-0-C H2CH3 H3O+ > PV J} H
O-CH 2 CH 3 H
ethyl orthoformate acetal aldehyde
Q. 5 Suggest a resonable mechanism for each of the following reactions:
(CH3)3Cx/Ox ||
.C CH, NaQCH3 (CH 3)3CCCH2OCH 3
Cr CH3OH (88%)
Q. 6 Predict the organic products:

O
2M
(a) CH 3 - C - C H 3 + H O - C H 2 - C H 2 - N H 2 " >

.CH 2 - CH 2 - CH 7 -NII 2
w
Q o " ^
o
(C) C - CH3 - COCb/NeOH/HDH )
\ / (ii ) H

Q.7 A synthesis that begins with 3,3-dimethyl-2-butanone gives the epoxide shown. Suggest reagents
appropriate for each step in the synthesis.
0 O OH 0
54% 68 %
(CH 3 ) 3 CCCH 3 ) 3 CCCH 2 Br >(CH3)3CCHCH2Br >(CH3)3 CC>—"cH2
H
Q. 8 Show how you would accomplish the following syntheses efficiently and in good yield. You may use any
necessary reagents.
O 0 0
(b)
(a)\ ^
CHO CH2OH CHO CHO
O CHCH2CH 3
CHO CHO
(,! i r - r r r « c r f - + c r i ?
Q. 9 Outline resonable mechanisms for each ofthe following reactions:
0
O
CH 2CH 2CH 2CH2Br KO C ( CH 3 ) 3
benzene
(76%)
Q. 10 IdentifyAtoD:
Me2CH - CH2 - CHO > (A) HN O 2 > (B) A > (G) H2O/H /A
+
> (D)
Q. 11 Gve the structures ofAto E in the given set of reaction:

O
S
HCN/OHS H 0/H /A_^ H 0 ( i ) BH / T H F
> ( A ) 2 ( B ) 2S 4 > ( c ) 3 >
CH3-C-CH3 (ii) CH3COOH
(i) BH3/THF I
(ii) H 2 O2/OH® I
(D)
Q. 12 Give the structure of the substance for each of the following reaction:
O
11
y
O
c- CH 3
(a) (X) NaOH/A > r 1 (b ) (Y) NaOH/A > / \\
CH
ISJ
(C) (Z)
o
Q.13 Each of the following reactions has been reported in the chemical literature. Write the structure of the
product (s) formed in each case.
(a)
(b) CI
Q.14 IdentifyAtoE:
CH^x /^ O
LSH <fy Conc, H 2 S 0 4 / A

H 2 / Pt * 0 )
(C)
Q.15 Identify Ato E in the given sequence of reaction;

O
SeQ2/CH2Cl2 ^ A ) CF3COOOH ) TR) H2Q > (C) NH3/A )( T>) (i)BH3/THF ) (p )
(ii) H 2 0 / H ®
Q. 16 Identify (A) to (E) in the given sequence of reaction:
CI W
BA0
I ^ S _ D M S O ^ ( A ) .(B) ^ . C ^ (C ) '",,A ' ( D ) ^ F ^ ( E )
K O H / A
l ^ J (ii)HOH
Q.17 Syntheses of each ofthe following compounds have been reported in the chemical literature. Using the
indicated starting material and any necessary organic or inorganic reagents, describe short sequence of
reactions that would be appropriate for each transformation.
(a) 1,1,5-Trimethylcyclononane from 5,5-dimethylcyclononanone
(B) H X / A V J FROM C 6 H 5 C
CH 3 CH 2
(c) R ^ V C CH 2 CH 2 CH 2 CH=CH 2 from o-bromotoluene and 5-hexenal.
u
ISJ
EXERCISE-III
Q. 1 Compound (A) C9H,0O is inert to Br2 / CC14 and on vigrous oxidation with hot alkaline KMn0 4 yields
benzoic acid. (A) gives red precipitate with 2, 4 DNP / HC1 / A.
(a) Write all possible structures of [A] and
(b) How can these isomers be distinguished by chemical tests?
Q.2 Compound (A) C8HgO is water insoluble and gives yellow precipitate with I2/NaOH. It reacts with NHÔH
in the presence of NH4C1 /NH4OH to give two geometrical isomers (B) and (C) having MF CgHgON.
These two compounds do not undergo dehydration. What will be structures of (A), (B) and (C) ?
Q. 3 A dithiane synthesis can convert an aldehyde to a ketone. The aldehyde isfirstconverted to its dithiane
derivative, which is deprotonated and alkylated. A mercuric chloride - assisted hydrolysis gives the
ketone. Show how this techinque might be used to convert benzaldehyde to benzyl phenyl ketone
Q.4 Wolff-Kishner reduction (hydrazine, KOH, ethylene glycol, 130°C) of the compound shown gave
compound A. Treatment of compound A with m-chloroperoxybenzoic acid gave compound B, which
on reduction with lithium aluminium hydride gave compound C. Oxidation of compound C with chromic
acid gave compound D (C9HI4 0). Identify compounds A through Din this sequence.
Q. 5
CO-
Reaction ofbenzaldehyde with 1,2-octanediol in benzene containing a small amount of p-toulenesulfonic
acid yields almost equal quantities of two products in a combined yield of 94%. Both products have the
molecular formula CI5 H22 U, Suggest reasonable structure for these products.
Q.6 The sex attrac tan t of the female winter moth has been identified as the tetr aen e
CH3(CH2)8CH=CHCH2CH=CHCH2CH=CHCH-CH2. Devise a synthesis of this material from
3,6-hexadecadien-l-ol and allyl alcohol.
Q. 7 Hydrolysis of a compound A in dilute aqueous hydrochloric acid gave (along with methonal) a compound
B, mp 164-165°C. Compound B had the molecular formula C)6 H I6 0 4 . Whatistheresonable structure
for compound B?
/^-CHCH(0CH3)2
OH
Compound A
Q. 8 When HO-CHJ-CHJ-CHJ-CHJ-CHO this compound is dissolved in water it exist in the equilibrium

ofisomeric forms. Both forms are ring-chain isomers. Write the structure ofisomeric cyclic form and
give mechanism for the formation of cyclic form. When (I) is treated with CH3OH in dry HC1 a new-
product (iii) is obtained. Give structure of this compound.
Q. 9 Compound (A) C5Hg, decolourises bromine water and on reduction with H 2/Pt gives compound (B)
having MF C5H!2 . A gives compound (C) with I V Lindlars catalyst and compound (D) with Na/NH3
(/). Compound (C) and (D) are isomers having MF C5HK). (A) on hydration gives two isomeric
compounds (E) and (F) having MF C5H10O. (E) gives yellow precipitate with 12 / NaOH but (F) does
not. What will be the structures of (A) to (F) ?
Q. 10 An organic compound (A) contains 40% carbon and 6.7% hydrogen. Its vapour density is 15. On
reacting with a concentrated solution of potassium hydroxide, it gives two compounds (B) and (C).
When (B) is oxidised, original compound (A) is obtained. When (C) is treated with concentrated HC1,
it gives a compound (D) which reduces Fehling and ammonical AgN0 3 solution and also gives
effervescences with sodium bicarbonate solution. Write structures of (A), (B), (C) and (D) and explain
reaction.
tBansal Clt Carbonyl Compound

EXERCISE-IV (A)
Q. 1 The formation of cyanohydrin from a ketone is an example of: [IIT1990]

(A) Electrophilic addition (B) Nucleophilic addition
(C) Nucleophilic substitution (D) Electrophilic substitution
Q.2 The enolicformof acetone contains: [IIT 1990]

(A) 9 sigma bonds, 1 pi bond and 2 lone pairs (B) 8 sigma bonds, 2 pi bonds and 2 lone pairs
(C) 10 sigma bonds, 1 pi bond and 1 lone pair (D) 9 sigma bonds, 2 pi bonds and 1 lone pair
Q.3 m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives: [IIT 1991]
(A) Potassium m-chlorobenzoate and m-hydroxybenzaldehyde
(B) m-hydroxybenzaldehyde and m-chlorobenzyl alcohol
(C) m-chlorobenzyl and m-hydroxybenzyl alcohol
(D) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol
Q.4 Hydrogenation ofbenzoyi chloride in the presence ofPd and Ba S0 4 gives: [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol
Q.5 An organic compound C 3 H 6 0 does not give a precipitate with 2,4-Dinitrophenyl hydrazine reagent and
does not react with metallic sodium. It could be: [ITT 1993]
(A) CH 3 CH 2 CH0 (B) CH3COCH3
(C) CH2 =CH-CH 2OH (D)CH 2 =CH-0-CH 3
Q. 6 Under Wolif Kishner reduction conditions, the conversions which may be brought about is?
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane
[IIT 1995]
Q.7 In the reaction, Pis [IIT 1995]

CH3 \
P + Se + IÔ
CH
(A)CH3 COCHO (B)CH 3 COOCH 3 (C) CH 3 C0CH 2 0H (D) None
Q.8 IntheCannizzaro reaction given below, 2Ph-CHO oh" ) Ph-CH 2 OH+ PhC0 2 the slowest step is:
(A) the attack of OH" at the carbonyl group
(B) the transfer of hydride to the carbonyl group
(C) the ab straction of proton from the carboxylic acid
(D) the deprotonation of Ph-CH,OH [IIT 1996]
Q. 9 Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
(A) MeCOCl (B)MeCHO (C) MeCOOMe (D) MeCOOCOMe
[IIT 1997]
Q 10 In a Cannizzaro reaction the intermediate which is the best hydride donor is: [IIT 1997]
H
O"

Q. 11 CH3CHO + H 2 NO H > CH 3 - CH = N - OH. The above reaction occurs at: [IIT 1997]
(A) pH = 1 (B) pH = 4.5 (C) Any value of pH (D)pH=12
Q. 12 Among the following compounds, which will react acetone to give a product containing > C = N -
(A)C 6 H 5 NH 2 (B)(CH 3 ) 3 N (C) C 6 H 5 NH C 6 H s (D) C 6 H s NH NH ,
[IIT 1998]
Q. 13 The product obtained via oxymercuration (HgS0 4 -H 2 S0.) of 1 -butyne would be
O
||
(A) CH 3 CH 2 - C - CH 3 (B) CH 3 CH 2 CH,CHO
(C) CH 3 CH 2 CHO + HCHO (D) CH 3 CH 2 COOH + HCO OH [IIT 1998]
Q. 14 Which of the following will undergo aldol condensation: [IIT 1998]

(A)Acetaldehyde (B) Propanaldehyde (C) Benzaldehyde (D) Trideutero acetaldehyde
Q 15 Which ofthe following will react with water: [IIT 1998]

(A)CHC13 (B)Cl 3 CCHO (C)CC14 (D) CICH2CH2CI
Q 16 A new carbon-carbon bond formation is possible in [IIT 1998]

(A) Cannizzaro reaction (B) Friedel-Crafts alkylation
(C) Clemmensen reduction (D) Reimer-Tiemann reaction
Q 17 The enol form of acetone, after treatment with D 2 0 gives: [II T 1999]
OD O OH OD
I II I I
(A) CH , - C = CH 2 (B) CD 3 - C - CD 3 (C) CH 2 = C - CH2 D (D) CD 2 =C - CD 3
Q. 18 Which of the following has the most acidic hydrogen: [IIT 2000]
(A) 3-hexanone (B) 2,4-hexanedione (C) 2,5-hexanedione (D) 2,3-hexandione
Q. 19 The appropriate reagent for the following transformation: [IIT 2000]
C I L 2 C I 1 3
° /V
v
ch3 • J. J
H 0
HO"
(A)Zn(Hg), HC1 (B ) H H 2 NH 2 , OH (C) H 2 /Ni (D) NaBH4
Q.20 A mixture of benzaldehyde and formaldehyde onheating with aqueous NaOH solution gives:
(A) benzyl alcohol and sodium formate (B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate (D) benzyl alcohol and methyl alcohol [ IIT 2001 ]
Q.21 Compound A (molecular formula C 3 H 8 0) is treated with acidified potassium dichromate to form a
product B (molecular formula C^HÔ). B forms a shining silver mirror on warming with ammonical silver
nitrate. B when treated with an aqueous solution of H2 NCONHNH 2 . HC1 and sodium acetate gives a
product C. Identify the structure of C.
(A) CH 3 CH 2 CH = NlN'HCONH2 (B) CH , - C = NNHCONH,
i
CH 3
(C) C H 3 -C = NCONHNH 2 (D) CH 3 CH 2 CH-NC0NHNH 2 [IIT2002]
CH,
ISJ
/CHO OHCN
' Q \ ( O \ ( i )N a OH ( ex c es s )1 0 0° C
Q.22 [IIT 2003]
(ii)H+/H20
s
CHO OHC /
any one of the products formed is :

/COOH HOOCv
(A)
COOH HOOC
CH 2 OH COOH
(C) OX—
COOH CH 2 OH
OCOCH3
Q.23 Acidic > Products formed by P & Q can be differentiated by: [IIT 2003]
Ô COC H, Hydrolysis
(A) 2, 4 DNP (B) Lucas reagent (Zn Cy conc. HCl

(C) NaHS0 3 (D) Fehlings solution
Q. 24 The order ofreactivity of phenyl Magnesium Bromide with the following compounds is [IIT 2004]
H
3 C
A (I)
C H
3 H, C
A (IT)
H Ph
A
(Til)
Ph
(D) All react with the same rate

(A) II > III > I (B) I > III > II (C) II > I > III
-COOH
'CHO
CH COONa
Q.25 +X 3 > [IIT 2005]
MeO
MeO
What is X?
(A) CH3COOH (B) BrCH2, COOH (C) (CH 3 C0) 2 0 (D) CHO-COOH
Q.26 The smallest ketone and its next homologue are reacted wi thN tÔH to form oxime.
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active [JEE 2006]

EXERCISE-IV (B)
Q. 1 C06 H3 5 -CHO + CH,J - COOC22H35 (d) | ITT 1995]

C. H. OH and heat
CH 3 CH 9 .
Q2 =Q C)kc n/ h2s °4 >D. [IIT 1996]
H (ii)LiAlH 4
Q. 3 Acetophenone on reaction with hydroxylamine-hydrochloride can produce two isomeric oximes. Write
structures ofthe oximes. [IIT 1997]
Q.4 An aldehyde (A)<CuHgO), which does not undergo self aldol condensation, gives benzaldehyde and
two mole of (B) on ozonolysis. Compound (B), on oxidation with silver ion, gives oxalic acid. Identify
the compounds (A) and (B). [IIT 1998]
Q.5 (a) Write the intermediate steps for each ofthe following reaction. [IIT 1998]
(i) C6H5CH(OH)C=CH > C6H5CH=CHC:HO
(ii)
Cf CH3
(b) Show the steps to carry out the following transformations.
(i) Ethylbenzene benzene
(ii) Ethylbenzene -» 2-phenylpropionic acid
Q. 6 (CH 3)2CHOCH3 HI(excess).heat ) (A) + (B) [IIT 1998]
J\J^ x h c 6 H 5 ^)LiAlH
[IIT 1998]
Q.7
a
(C)
( i i ) H + , heat
Q. 8 What would be the major product in each of the following reaction? [IIT 2000]
^Ph
Q. 9 Identify (A), (B) and (C), and give their structures. [IIT 2000]
0
-> A+B
L f — C (C 7 H ]2 0)
Q. 10 Five isomeric para-disubstituted aromatic compounds A t o E with molecular formula C 8 H g 0 2 were

given for identification. Based on the following observations, give structure of the compounds.
(i) Both A and B form a silver mirror with Tollen's reagent; also, B gives a positive test with FeCl3 solution
(ii) C gives positive iodoform test.
(iii) D is readily extracted in aqueous Na HC0 3 solution.
(iv) E on acid hydrolysis gives 1,4-dihydroxybenzene. [IIT 2002]

Q. 11 Write structures ofthe products A, B, C, D and E in the foliowing scheme. [IIT 2002]
O
^^
r^ A CH2CH2CH3 Cl2/FeCl3Â_NgL^B HN0 3 / H 2 S 0^ q
CH„=CHCH.,CrNa + H2/Pd/C
^D-
Q.12 C6HI2 _H£L > C 6 H 13 C1 (C)

(A) (B)
I Ale. KOH ^ ^ ozonolysis ^ ^

ozonoi sis
(A) y „ (F) + (G) NaOH ) HCOONa + 1° alcohol
(D) is isomer A. E gives negative test with Fehling solution but gives iodoform test. F and G gives Tolleris
test but do not give iodoform test. Identify Ato G [IIT 2003]
Q. 13 An organic compound (P), C 5 H u ,0 reacts with dil. H 2 S0 4 to give (Q) and (R). Both (Q) and (R) give
positive iodoform test. The reactivity of organic compound (P) is 1015 times more than ethylene with
respect to dil. H 2 S0 4 . [IIT 2004]
(i) Identify the compounds (P), (Q) and (R).
(ii) Give reason for the extraordinary reactivity of compound (P).
Q.14 -»X (i)O, .Y NaOH [IIT 2005]

(ii) Zn / CHj COOH
Identify X and Y.
Q. 15 Which of the following disaccharide will not reduce Tollen1 s reagent? [IIT 2005]
. HOH 2 C CH2OH
CH2OH CH2OH OHJ—O H H O—IOH
H
—9 /H H\ J oho •KHHCK Xonm
(a) ^ ^ (b) H — O — H
OH H H OH
OH H ^ OH H
(P)
fa Bansal Classes Carbonyl Compound

[21]
ANSWER KEY
EXERCISE-I(A)
Q.l C Q.2 B Q.3 C Q.4 A Q.5 D Q.6 B Q.7 C

Q.8 A Q9 B Q.10 B Q. ll C Q.12 B Q.13 A Q.14 A
Q 15 B Q.16 B Q.17 C Q.18 D Q.19 C Q.20 D Q..21 C
Q.22 C Q.23 A Q.24
Q.29 A Q.30 D Q.31 C
D Q.25
Q.32 B
A Q.26
Q.33 C
C Q.27
Q.34 D
D Q.28
Q.35 C
B
Q.36 B Q.37 D Q.38 D Q.39 C Q.40 D Q.41 C Q.42 A
Q. 43 B Q.44 C Q.45 B Q.46 B Q.47 C Q.48 A Q.49 C
Q.50 B
EXERCISE-KB)
Q.l C,D Q.2 B,C Q.3 A,C,D Q.4 A,B

Q.5 A,B,C Q.6 A,B,C,D Q.7 A,B Q.8 B,D
Q9 A,B,C,D Q.10 B,C Q.ll B,D Q.12 A
Q.13 D Q.14 A Q 15 A,B,C Q.16 A,B
Q.17 B,C,D Q.18 A,C,D Q.19 A,B,C Q.20 A,D
Q.21 A,C,D Q.22 A,B,D Q.23 A,D
Q.24 (A) P, R, (B) P, (C) S, (D) Q,S Q.25 (A) P, (B) Q,S, (C) S, (D) P
Q.26 (A) P, (B) Q, (C) S, (D)R
EXERCISE-II
Q.l (a) CH 3 -CH2-CH2 -OH (b) C H ^ C H ^ O ^ - O H

OH
(c) CH 3 -CH 2 -CH 2 -0 H (d) CH3 - CH 2 - CH - CH 3
OH OH
(e) CH3 - CH 2 - CH - C = CH (f) CH 3 - CH 2 - CH - (CH) 4 - CH 3
(g) CH 3 - C H 2 - C H - O C H , (h) CH3 - CHJ - CH ^ J
OH
H
(i) CH 3 -C H 2 -CH -NH- PH (j) CH3 - CH 2 - CH - N - CH ,
!
CH 3
(k) C- C- C= N- OH (1) CH 3 -C H 2 -CH=N-NH 2

(m) CH 3 -CH 2 -CH 2 (n) p-Nitro phenyl hydrazon
(o) semi carbazane (p) CH ,- CH 2 -CH=CH-CH3
OH
(q) CH 3 - C H 2 - C H - C N (r) C H 3 -CH 2 -C0 2 H
l&Bansal Classes Carbonyl Compound

http://slidepdf.com/reader/full/bansal-classes-organic-chemistry-study-material-for-iit-jee- [26]
o
Q.2 (a) C-C-C-C-OH (b) CH , - CH 2 - CH 2 - CH = C - CH 2 - CH ,
OH CHO
(c) C-C-C-C=N-OH (d) C - C - C - C - P h
OH
(e) Ph - CH = C - CH 2 - CH 3 (0 C - C - C - C H - C = CH
I
CHO
( g ) C- C - C- C < ° ] (h) C-C-C-C
(i) 2°alcohol (j) Cyclohydrides
OH
(k) 2° alcohol (1) CH 3 - C H 2 - C H 2 - C H - C H - C 0 2 E t
Et
Q.3(a) 3 > 2 > 1 > 4
OH OH
i
Q 3(b) (I) (CH 3 ) 2 CCN (ii) C 6 H 5 CCN
CH 3
Q.4 R-Mg-X
Q.6 (a) C H 3 - C H - N H - C H 2 - C H 2 - O H (b)

CH,
(c)CHCl3 + ^ ^ - C - O H
Q.7 HO®/Br2 : H 2 / Ni ; NaOH
Q.8 (a) (i) KM n0 4 , (ii) CH 2 - OH , (iii) LiAlH 4, (iv) H 3 0®
C H 2 -OH
(b) (i) CH 2 - O H , (ii) NaBH 4 , (iii) H 3 0 + , (c) (i) CH 2 - OH, (ii) PH 3 P=CH-Et
C H 2 -OH C H 2 -OH
(d) (i) H 2 , (ii) Ni; (e) (i) H2s (ii) Pd-C ; (f) NaBH 4
NH. OH
Q. 10 (A) Me 2 CH - C H . - C - CN (B) Me 2 CH - CH 2 - CH - CN
H
faBansal Classes Carbonyl Compound

[23]
OH
(C) Me XH - CH, - C H - C0 2 H (D) Lactide
OH OH
Q. ll (A) CH 3 - C - C H 3 (B)CH3-C-CH3 ( C ) C H 3 -C = CH 2
CN CO2H CO2H
Q.12 (a) (X) | CH,^

C C-CH3
U CH, a CHO
CH 2 -C=CH
o
1(
o
3
_ _ / S - C H 2 -OH Ph
CH - PH
(a) CH 3 -/ Y=c<PH <b) fO
cr
O
CO,H
Q.15 (A) (B) (C)

M:O,H
Q.16 (A) (B) (C) CHJ-CHJ-CN
F CH2 — CH2
(D) f >- C- C- C0 2 H
CO2H
Q.17 (b)CH 3 MgBr/ H\ A

CH 3 o
+ H-C-C- C-C =C
(0 o
L(0 M 8 i (iii) PCC
(u )H ' (iv) Ph3 P=CH3
EXERCISE-HI
Q. l Possible structure an
(A) Ph-CH 2 -C H 2 -CHO (B ) Ph - CH - CH 3
CHO
Carbonyl Compound
[23]
faBansal Classes
(C) Ph-C-CH 2 - C H 2 (D) Ph-CH 2 - C - C H 2
O
o
.2 Ph - C - CH , Ph-CH=CH-CH 2 -OH
Q.4 (A) (B)o:

(oH0 Oo
(D)
Q.5 PIK • O- CH ,
c I "
H" 0-CH-(CH2)5-CH3
Q.7 Ph—CH—CH—OH
/ \
o o
\ /
CH-CH
OH Ph
Q.8 OH OCHoJ
I I
CH- CH—
I I
CH 2 CH 2
CH 2
I
O I
CHO o
CH 2? I
I CH7-
CL IO -
(a &(3)
Q.9 (A) C- C= C- C-C (B) C- C- C- C- C (C) cis C- C= C- C- C (D) Trans C- C= C- C- C

O
(E) C - C - C - C - C (F) C - C - C - C - C
il
0
Q.10 Empirical formula of (A) = 0 ^ 0 ;
Molecular formula of (A) = CFIjO
HCHO CH 3 OH HCO OK HCOOH
Methanal (A) (B) (C) (D)
EXERCISE-IV (A)
Q. l B Q.2 A Q.3 D Q.4 B Q.5 D Q.6 D Q.7 A

Q.8 B Q.9 A Q.10 D Q. ll B Q.12 A,D Q.13 A Q. 14 A,B,D
Q. 15 B Q.16 B,D Q.17 B Q.18 B Q.19 B Q.20 A Q.21 A
Q.22 C Q.23 D Q.24 C Q.25 C Q.26 B
l&Bansal Classes Carbonyl Compound [29]
EXERCISE-IV (B)
Q. 1 C6H5CH = CHCOOC2H5
(D)
CH3ch2x^ ÔH
Q 2 Cx
H /" CH2NH2
(a racemic mixture)
Q3 C6H5-C-CH3 and C6HS-C-CH3

II ' II
N-OH HO-N
s n
Y anti (isomers)
CH=CH-OC-CHO
Q.4 [Ol Ozonolysis > fO f H

° + COOH
C 0 0 H
X ) ^ COOH
(B) (Oxalic acid)
Q.5 (a) (i) C 6 H 5 CH(OH)OCH C 6 H 5 CH-C = CH

-H,0
OH^
C6H5CH=CHCHO v TautomerisatioiT C6HSCH=C= CH C6 H5CH=C= CH
OH
+
'CH,
— A
C H C H
1\ uv e ess),
HI 3\
Q.6 _ >HOCH 33 ^ Af >_ p C H L + CHgl
CH,/' 'CH,
CHC 6 H 5
C fi HcC HO I 7
Q.7 >
ase
+Base
(C) (D)

o o
CH3 /CH3
Q.9 C- CH 3 Br2+NaOH ^ f "j ^C OO Na + C H B r 3
(A) (B) (C)
o
CHO CHO CH ? OH Mo t t COOH 0-CH =CH 2
C—CH3
Q.10 (A) ( O ) or [ O ] (B )[ 0] ( C ) ^ O O f O l ^ l O
OCH3 CH 2 OH OH CH 3 OH
OH
NO, NO ,
Bu Bu
Q.ll (A) (C) c r y (D)f c\-

v_
C1 O-CH 2 - CH=CH 2
(E)
O-Pr
Q. 12 Me3C-CH=CH2 _HO_>Me2C -CHMe2 + M e 3 C - C H - M e
CI CI
( A) ( B) ( C)
ale. KO H
( A) Ozonolysis ) HCHO + MejC-CHO NaOH ^
(F) (G)
H C O O N a + M e g C - C H j O H ( l ° a l c o ho l )
CH 3
Q.13 C 5 H 1 0 Ois H 2 c < A o /\ C H 3
CH 3 CH,
CH, I
x+ H,0 + C2H5OH
^ O R CH.
H- H3C 0' CH3 ) H 3 C" "O
Highly stable car boctaion
P is stabilized by resonance
^Bansal Classes Carbonyl Compound [31]
(X)
Q . 15 In structure (P) both the rings are present in acetyl form therefore it will not hydrolyse in solution that why
Fehling solution cannot react with this.
In structure (Q) one ring present in the form of hemiacetal. This will hydrolysed in solution it can reduce
Fehling solution.
I BANSALCLASSES
* TARGET IIT JEE 2007
ORGANIC CHEMISTRY
XII (ALL)
CARBOXYLIC ACIDS AND

ITS DERIVATIVE,
ALIPHATIC AMINES
CONTENTS
EXERCISE-I
EXERCISE-II
EXERCISE-III
EXRECISE -IV(A)
EXRECISE-IV(B)
ANSWER KEY
EXERCISE -1(A)
Q.l Which one ofthe following is an acyl group:

o o o
(A)R-O- (B ) R- C- O - (C )R -C - (D) R - C - N H -
O
(i)Bf2/K0H
C6HS-C-CH3 >CHBr3 + [X]
6 5 3
(ii )ir
[X] will be:

(A)C 6H5-CHO (B)C6H5COOH (C) CgHj-CRjOH (D)CH3COOH
CH3-CSC-H CH 3 MgBr ) C H + ( A } ^ ) ( B )
3 4
( i i ) H 2 0/ H ®
(B) will be:

(A) CH 3 -OC-CH 3 (B) CH3-C=C-MgBr '(C) CH3-CSC-COOH (D) CH3-CH=CH-COOH
Q.4 Consider the given reaction •
RCOOAg Brz/A >R-Br

which one of the following acid will give maximum yield ofR-Br in the above reaction?
(A) CH3 - CH - COOH (B)CH 3-CH 2 -CH 2 -COOH
CH3
CH3
(C) CH 3 - C - C O O H (D) All will give same yield
CH3
Q. 5 Benzoic acid on treatment with hydrazoic acid in the presence of concentrated sulphuric acid gives:
(A) Benzamide (B) Sodium benzoate (C) Aniline (D) C6H5CON3
C H CH
2 5 2 5
I N,H/Conc.H,SO, r l T n MXJ
CH3-C-COOH— ^-^CH3 - C - N H2
C 3H 7 C 3H 7
is called:
(A) Schmidt reaction (B) Cirtius reaction
(C)Hofinann rearrangement (D) Lossen rearrangement
<fIBansal Classes Carboxylic Acids & It's Derivative Aliphatic amines Page # 2
CH3-CH2-COOH ^)AgN°3 > [X]
(ii)Br 2 /A
[X] will be:
(A) Ethyl bromide (B) Propyl bromide (C) Propyl propanoate (D) All of these

CH3 - CH - COOH — [ Y ]
I
OH
[Y] will be:
(A) CH3 -CH-C=0 (B) CH2=CH-COOH
o
OH n
(C) CH2 - CH2 - COOH (D) CH3-CH CH-CH3
W
o
Q. 9 Acetylation reaction with acetyl chloride is carried out in the presence of which solvent?
(A)HOH (B)CH3OH (C) Pyridine (D) NaOH
Q.10 In the reaction:

O
C6H5 H C H
" St? 6 5 ~C-CH2-C6H5
[X] will be:
(A) CgHsCHjCOCl (B) (C 6 H 5 -CH 2 C0) 2 0
(C) Both (A) and (B) (D) C6H5-CHC12
Q.ll In the given reaction:

[X] + Acetic anhydride > Aspirin
[X] will be:
(A) Benzoic acid (B) o-methoxybenzoic acid
(C) o-Hydroxybenzoic acid (D) /?-Hydroxybenzoic acid
Q.12 The given reaction is:
C6H5-CHO + C6H5CHO Na2[Fe(C0)4] > C6H 5 - fi-0-CH2C6H5

(A) Claissen reaction (B) Tischenko reaction(C) Perkin reaction (D) Cannizzaro reaction
Bansal Classes Carboxylic A cids & It's Derivative Aliph atic amin es Page #3
0 O
c2H5QNa >
[X]
C 2 H 5 OH
[X] will be:
OH O O
I!
(A) C-CH2-C-CH3 (B) HC = CH - C - CH,
H
o
(C) C H 3 - C - C H 2 - C - | ^ J ' (D) CH 3 - C - C H 2 - C O O H
Q.14 Number of cross products in the given reaction:

CH3COOC2H5 + C6 H5-CH 2 -COOC2 Hs c
2 h 5° HL
C 2 H 5 OH
(A) One (B) Three (C) Two (D) four
Q.15 Hofmann degradation is given by:

(A)Imide (B) Acid chloride (C) Acid anhydride (D) None of these

O
'CH3 L,MH4 )[X]
C6 H5-C-N
-CH 3
[X] will be:
-CH,
(A) C6 H5-CH 2 OH (B)C6 H5 COOH (C)C6H5CONH2 (D) C 6 H5 -CH2-N:
-CH,
Q.17 Which one of the following compounds gives carboxylic acid with HN0 2 ?
O
( A ) C 6 H 5 -C -C 1 (B) C6H5CONH2
(C) C H 3 -0C - O - C
fl- C H 3 (D) CH3COOC2H5
fe Bansal Classes Carboxylic Acids & It's Derivative Aliphatic amines Page #4
Q .18 In the reaction sequence:

O
H2 /Hffi
CH, - C - H - ^ - K A ) ° > Product
A
OH
Product will be:
OH
(A) CH3-C-COOH
H
OH
(B ) HOOC -C -C H 3
1
I
H
OH OH
(C) Mixture of CH - C - COOH and HOOC - C - CH
3 3
H H
OH
(D) CH 3 - C H - C O N H 2

CI
(l)NHs
CH - CH - COOH > [X]
3 Imole
(ii)H20
Product [X] will be:

(A) a-Amino acid (B) a-Aminoamide (C) P-Amino acid (D) 3-Aminoamide
Q.20 Which of the following reactions will give a-hydroxy acid as a product:
(i)NaCN/HCl
(A) CH 3 -CHO —(i)NaCN/HCl )
( i i ) H2 0/H®/A
(i)Zn
(B) CH 3 -CHO + Br-CH 2 -COOC 2 H,
(ii )NH 4 C l / H O H
(iii )HOH/ H® / A
X
(C) CH 2 - CH 2 - COOH NaOH /HOH ^
(D) All of these
Q. 21 Rochelle salt is dimetal salt of:

(A) Tartaric acid (B) Citric acid (C) Oxalic acid (D) Salicylic acid
< f I B a n s a l Classes Carboxylic Acids & It's Derivative Aliphatic amines Page # 5

OH
•COOH
O ]
[X] will be:

CI OH CI
•COOH
C0Cl
(A)[OT (B) -(C) L O J ^ > (D) CQC
Q.23 Sodium bicarbocate reacts with salicylic acid to form:

OH ONa ONa
A . .COONa A. A.
B C00H
(A)C 6 H 5 ONa ( )[pT (C)[pJ (D)(cTpC0 0N a

OH
A^COOU
200 c
f QJ ° ) [X]
[X] will be:

(A) Phenyl salicylate (B) Aspirin (C) Phenol (D) Benzoic acid
Q.25 Arrange these esters in decreasing order of ease of esterfication with CH, OH/H®:
(I) CH , - CH - COOH (II) CH 3 - CH - CH 2 - COOH
i I
CH, CH 3
CH 3
(III) CH, - C - C O OH (IV)( CH,-C H 2 ),C-COOH
CH 3
(A) 11 > 1 > III > IV (B) I > II > 111 > IV (C) III >IV > II > I (D) IV > 111 > II > I
Q.26 Arrange following compounds in decreasing order of reactivity for hydrolysis rea ction:
(I)C 6 H 5 COCI (II) N O 2 - { O ) - C O C I
(NI)CH3- / R ) Y C O C I (IV)OHC-\OVC-CI
(A) II > IV > I > III (B) II > IV > III > I (C) I > II > III > IV (D) IV > III > II > I
Q.27 In the given reaction sequence:
B
CH,-CH 2 -OH (^Mn0 4 /8 H /A VKOH
3 2
(ii)H® (ii)NH3/A
(C) will be:
(A) Methylamine (B) Eltylamine (C) Propylamine (D)Acetamide
Q.28 Which one of the following on heating gives unsaturated acid:
(A) a-Hydroxy acid (B) P-Hydroxy acid (C) y-Hyroxy acid (D) 5-Hydroxy acid
Q.29 Which will form lactone on treatment with NaOH?

(A) a-Bromo acid (B) p-Bromo acid (C) P-Hydroxy acid (D) 5-Bromo acid
Q. 3 0 Which one ofthe following will go decarboxylation on heating?

(A) Succinic acid (B) Phthalic acid (C) Malonic acid (D)Adipicacid
Q. 31 In the given reaction:
(L)BF2/P
CHJ-COOH
6 > [X]
(ii)NaCN
(iii)H20/H®/A
[X] will be:
/C OOH
(A) CH , . (B) COOH CHL-CH,-COOH
^COOH
CH2-CO\^ /CO \
Q. 3 2 Which optically active compound on reduction with LiAlH4 will give optically inactive compound?
(A) CH3 - CH - COOH (B) CH 3 - CH 2 - CH - COOH
I 3
OCH I
OH
(C) CH3 - CH 2 - CH - COOH (D) CH 3 - CH - CH 2 - COOH

I I
CH 2 OH OH
O
CH 3 - CH - C - CHR - CH, CF3CQOOH .
, 2 3 * [X] as main product
[X] will be:
O O
II II
(A) CH3 - CH 2 - C - O - CH - CH 3 (B) C H 3 - C H - C - O - C H 2 - C H 3
CH 3 CH 3
0
(C) CH 3 - C - OC(CH 3 ) 3 (D) (CH 3)3COOCH 3
(fe Ban sal Classes Carboxylic Acids & It's Derivative Aliphatic amines Page # 7
Q. 3 4 Which one of the following reactions can be used for the preparation of (3-hydroxy acid:
(A) Perkin reaction (B) Reformatsky reaction
(C) Aldol condensation '(D) Claisen condensation
Q.3 5 Which acid can be oxidised be Fehling solution:

(A) Malonic acid (B) Acetic acid (C) Oxalic acid (D) formic acid
Q.3 6 In the given reaction:
COOH
[X]
0
[X] will be:
COBr COOH OOH COOH
Br
(A)
0 «CJ
(C) (D)
0
Q. 3 7 Reducing property offormic acid is due to the presence of:
O O
II II '
(D) All of these
(A) - OH (B) - C - H (C)-C-OH
O
A o ,
+ [X]
•CH,
[X] will be:

OH
(A) HOOC-CH2-CH2-CH -CH3 (B) CH 3-CH2-CH2-CH2-COOH
(C) HO-C^- CI^-CI^-COOH (D) CH3 - CH2 - CH - CH2 - COOH

I
OH

O
LlAm
° * > [A]
Na BH 4
[B]
[A] and [B] respectively be:
(A) CH2 OH - CH 2 - CH 2 - CH - CH2 OH and I I
OH t)H
(B) f j and C H2 OH - CH, - CH2 - CH - CH 2 OH
OH OH
o
A
(C) Both are I J
OH
OH
(D) Both areC H.OH - CH2 - CH 2 - CH - CH 2 OH
2
C H ^ " C°OC2H5
p
+ I y"dne > [X]
cooc
CH2^ NH2 A
[X] will be:
H
H N o
(A)[ 7 (B)kN>0
I H
H
/COOC2H5
"N=Cv-C00C2H5
N=c /COOC2H5 CH2
ÔOC 2 H5
(C)[ (D)CH2
/COOC 2H5
-NHO v M r
iN =
^-COOC^Hg
^B ansa I Classes Carboxylic Acids & It's Derivative Aliphatic amines Page # 9
Q. 5 0 The treatment of an ester with LiAlH4 followed by acid hydrolysis produces :
(A) Two aldehyde (B) One carboxylic acid and one alcohol
(C) Two alcohols (D) Two acids
Q. 51 Which of the following is hydrolysed to give secondary amine:

<jj .CH3
(A) Alkyl cyanide (B) H - C - N '
-CH3
(C) Nitro paraffins (D) Acid amide
Q.52 N-Ethyl pthalimide on hydrolysis gives:

(A) Methyl alcohol (B) Ethyl amine (C) Dimethyl amine (D) Diethyl amine
Q.53 Which amine will not react with nitrous acid:

(A) Methyl amine (B) Ethyl amine
(C) Dimethyl amine (D) N, N Dimethyl ethane amine
Q.54 Which gas will be evolved out when [CHÔ-LNT^ + (CH3)2CHNH2] is treated with sodium nitrite and
HCl:
(A) Chlorine (B) Ammonia (C) Nitrogen (D) N0 2
Q.55 Boiling Ethylamine on reaction with acidified KMn04 gives:

(A)Acetaldehyde (B) Ethanoic Acid (C) Ethanol (D)Acetamide
Q. 5 6 Methyl amine on reaction with chlorine in the presence ofNaOH gives:

(A) Chloroform (B) Methyl chloride
(C) N-Methyl chloramine (D) Chloramine
Q.57 Highest value ofpK b will be of:

(A)NH3 (B)(CH3)2NH (C)(CH3)3N (D)CH3NH2
Q.58 Lowest boiling point will be ofthe compound:

(A) Ethylamine (B)Ethylmethylamine
(C) 1-Propaneamine (D) N,N-Dimethylmethaneamine
Q.59 Amines are basic in nature because:

(A) They produce OH ions when treated with water
(B) They have replaceable H atoms onN atoms
(C) They have 1 one pair of electron on N atom
(D) None of these
Q.60 Which ofthe following diazonium salt is relatively stable of 0-5 °C:
(A) CH3-N=N}®C1- (B) CH3C(CH3)-N=N}®C1-
(C) C6H5-N=N}®CL (D) (CH3)3C-N=N}®C1-
Q. 61 Alkylamine dissolve in hydrochloric acid to form alkylammonium chloride. The nitrogen in the latter salt is:
(A) Quadricovaient only (B) Tricovalent only
(C) Unielectrovalent only (D) Quadricovaient, Unielectrovalent
Q.62 Which of the following can be detected by carbylamine reaction:

(A) Urea (B) CH3CONH2 (C) C ^ N f ^ (D) All of above
Q. 63 Cyanides exists in:
(A) Tautomeric form (B) Geometrical form (C) In both form (D) None
Q.64 Hydrolysis ofalkylisocyanide yields:
(A) Primary amine (B) Tert. amine (C) Alcohol (D) Aldehyde
Q. 6 5 Which of the following compound gives the smell of mustard oil:
(A) Alkyl isocyanate (B) Alkyl isothiocyanate
(C)Alkylisocyanide (D) Alkyl isonitrile
Q. 66 The compound obtained by the reaction between primary amine and aldehyde is:
(A) An amide (B)lmine (C) Nitrite (D) Nitro
Q. 6 7 When propionamide reacts with Br2 in the presence of alkali the product is:
( A) CH3CH2CH2NH2 (B)CH3CH2NH2 (C)C3H7CN (D) C2HsCN
Q.68 A reaction of ethyl amine & acetic anhydride leads to the formation of:
(A) CH3NHCOCH3 (B) C2H5CONHCH3 (C) CH3CONHC2H5 (D) CH3-CH=NOC2H5
Q.69 Identify X in the reaction
JJ —CHCI3 /KOH ^ Intermediate ———^ X

heat 300K
CI
COOH NH 2 NC NH 2
« J (B )0 (C ,0 . ( D , 0
CI CO OH CI CI
C6H5-NHX
Q.70 g cone HC1 > A + fi
C6H5-NH^ Heat
The unknown compounds A and B in the above reaction are:
(A) Phenyl mercaptan and aniline (B) Thiophenol and aniline hydrochloride
(C) C 6H 5 -N=C-S and C 6H 5 NH3} CI (D) C6H5CH2SH and C 6 H 5 NH3} CI
Q.71 Aniline with solid KOH and CS 2 gives:

(A) Thiourea (B) Phenyl thio urea (C) Phenol (D)Diphenyl thiourea
Q CH3MgBr
Q.72 rI V/ c N H
z Â W H3O >X O'^vppt.)
Ca(OH ) 2,I 2
Zis:
O
(A) [ C - CH3 (B) [ > C O O H
(C)
(i)N 3 A
Q.73
V
Y < ^ ^ - < f Q V c O O H ° ' > X, What are X and Y.
(")KOD,Br 2 A (ii)KOH,Br 2 A
(A) X is Yis ( O ^
(B) X is < ( ( ^ N D 2 ; Y : i s <0/^NH 2
(C)both <(C?)-ND 2
(D) both < ^ O y ~ N H 2
Q.74 Major end product of the following sequence of reaction is:

CH3CH2CH2CONH2 - ea( O H ) 2> C I 2 ) X _ J ! N O 2 _ > Z
(A) CH3CH2CH2NH2 (B) CH3CH2CH2OH
(C) CH3CHCH3 (D) CH3CH2COOH

OH
Q. 75 The bond angles in methane (I), ammonia (II) and trimethyl amine (III) increase in the order:
(A) I >111 >11 (B) I >11 >111 (C) II > I > III (D) III > II > 1
Q.76 Name the products in the acid-base reaction:

(a) CH3CH2NH2+ HI (b )(CH3)3N + HBr
(A) (a) Trimethyl ammonium iodide (b) Trimethyl ammonium bromide
(B) (a) Ethyl ammonium iodide (b) Methyl ammonium bromide
(C) (a) Ethyl ammonium iodide (b) Trimethyl ammonium bromide
(D) All of these
Q. 77 Acetic anhydride and ammonia gives the product:

(A) CH3C0NH2 (B) CH3CONHCH3 (C) CH3CN (D) CH3COONH4
Q. 78 The artificial sweetener aspartame (A) is converted to on storage for extended periods of
time in aqueous solution: ^ Q
H 3 N - C H - C - N H - C H - C-OCH3
CH 2 CH 2 Ph
(A)
O O
I! II
(A) H 2 N - C H - C - N H - C H - C - O C H 3
CH 2 CH 2 Ph
CO.
H 2 N - CH - COH + H2 NC H - COH + CH 3OH

CB)
W I I
CH 2 CH 2 Ph
CO 2 H
O^nh^ci^COV
(C)
Dkru
1
PhCH2 / ^ N H ^ - Q I + CH3OH
(D) no change, remains as (A)
Q. 79 Reductive amination ofAforms:
(A)L V (C)ULnhJ
Q. 8 0 The synthetic sweetener aspartame, known commercially as Nutra sweet, is carboxylic acid. In aqueous
solution on standing it changes to:
(AA >
( C ) \\ /F NH
\ //
EXERCISE - KB)
Q. 1 Consider the following statements regarding the following reaction:

(CH,CO),
3 2O H,-0
2
QHXHO
6 5
—> —> Cfi6 H,-
5
CH = CH - COOH + CHXOOH
3
CH3COONaA
(A) Acetate ion acts as base in this reaction

(B) The anhydride having atleast one a-hydrogen, provides an enolate for the reaction
(C) The acetate deprotonates the anhydride to form the nucleophile needed for the reaction
'(D) EtONa can also be use as base
Q.2 Which of the following will liberate C0 2 on reaction with NaHC03

O H
(A) ( 0 ) ^ ( B ) CH3COOH
CVO CH-CH2OH CH,OH

(C) T Y 4h (D> I 2
CH o 0H
HO HO
1
Q.3 RCOOR can be prepared by:
(A) esterification of RCOOH
(B) esterification of (RC0 ) 2 0
(C) Baeyer-Villiger oxidation of RCOR' withperoxy acid
(D) reaction of RCOCl with R'OH
Q.4 In the Hofinann bromamide degradation recation

?
R - C - N H 2 + KOH + Br2 >

Intermediates are:
(A) RCONHBr (B)RNCO (C) RNHj (D)None
Q.5 C4HJJN + HN0 2 > C,H ]0 O (3° alcohol)

(X)
hence X will give:
(A) carbyl amine reaction
(B) Hofmann mustard oil reaction
(C) diazonium salt (as the intermediate) withHN02
(D) base insoluble product with Hinsburg reagent
Q.6 Mixture of 1°, 2°

(A) Hinsberg's and 3° amines can be separated
method by:
(B) Hofinann's isocyanide test
(C)fractionaldistillation (D) Na N0 2 HCl
Q.7 Which is/are correct reactions):
(A ) CI + N H 3 —>ONH 4 CI
(B) y ^ C l + 2NH3 > y — m i 2 + NH4C1
( C ) ^ — CI + N H 3 — < ^ + N H 4 C I
(D) + HN0 2 ^
Q. 8 Which of the following compounds will give acetic acid with KMn04/H®/A:
(A) CH3-CHO (B)CH 3-CH=CH-CH3
(C) CH3-C=C-CH3 (D)CH3CH20H
Q.9 Acetic acid can be used for the preparation of:

(A) Ethane (B) Methane (C) Acetone (D)ethanol
Q.10 Which one ofthe following acids will form acetyl

(A) MeCOOH (B)chloride
MeCOOMewith PC15?
(C) MeCOOCOMe (D) Me-CONE^
Q.ll Consider the following reaction:
H
ff
CH3-C-OH+CH3-QH > C H , - C - O - C H 3 +HOH
True about the above reaction is:
(A) Product is having smell like fruits
(B) Nucleophilic addition followed by elimination reaction
(C) folio ws A ac , mechanism
(D) it is irriversible reaction

RCOOAg + X2 — R - X + C 0 2 + AgX
X2 can be:
(A) Cl2 (B)Br2 (C)I2 (D)F 2
Q.13 Which one of the following compounds will give HVZ reaction?
COOH
-COOH
(C) /-COOH
Q.14 Sodium salt of which one of the monobasic acids on electrolysis does not give hydrocarbon:
(A) C6H5COOH (B)HCOOH
(C) Me3C-COOH (D) COOH-CH=CH-COOH
Q.15 Which one of the following acids undergoes decarboxylation on strong heating:
(A) Pyruvic acid (B) 3-butenoic acid (C) Formic acid (D) Salicylic acid
Q.16 Which one ofthe following compounds is least reactive with water?
o o o o
(A) CH3 - C - CI (B)C6H5-C-NH2 (C)CH3-C-NH2 ( D ) C 6 H 5 -C-C1
Q.17 Acetic anhydride is used as:
(A) Solvent (B) Dehydrating agent (C)Acetylating agent (D)Anticeptic

O
II [X]
-» R - C - O - CFL
R-C-OH
[X] will be:
(A)CH2N2 (B)CH3OH/H® (C) MeCOOH (D)Me 2 S0 4
Q.19 Which ofthe following gives silver mirror test?

(A) HCOOH (B) CH3COCHOHCH3
(C) Tartaric acid (D) Glucose
Q.20 An example of a primary amine is:

(A) n-Propylamine (B) Isopropylamine (C) t-Butyl amine (D) Sec. butyl amine
Q.21 Which compound is soluble in water:

(A)[(CH3)2NH2]+C1- (B) [CH3NH3] CI
(C)[(CH3)3NH]'CT (D)PhN0 2 ~
Q.22 Which compound will liberate C0 2 from NaHC03 solution:

(A)CH3CONH 2 (B) CH3NH2 (C) (CH3)4N+OH~ (D) CH3N+H3C1"
Q. 23 Which of the following compound can be produced if 1 -propane amine is treated with NaNO, and HCl
(A) Propane-l-ol (B) Propane-2-ol (C) 2-Chloropropane (D) 2-Propaneamine
Q. 24 Which ofthe following amine does not react with Hinsberg reagent to give base soluble product
(A) Neopentvl amine (B) secpropyl amine (C) diethyl amine (D) Ethyl methyl amine
Q 25 Ethylamine can be prepared by

(A) Curtius reaction (B) Hofinann reaction (C) Mendius reaction (D)Reduction offormaldoxime
Q.26 The presence of primary amines can be confirmed in laboratory by:

(A) Reaction with HN0 2 (B) reaction with CHC13 and ale. KOH •
(C) Reaction with Grignard reagent (D) Reaction with acetyl chloride
Q.27 Select correct statement (s):
(A) Cyclohexanone is oxidised to caprolactone which is hydrolysed under the reaction conditions
(B) Baeyer-Villiger oxidation involves migration of H/alkyl/aryl groups which is in order H > tert-alkyl >
sec-alkyl > phenyl > primary alkyl > methyl
(C) Pinacolone (CH 3 ) 3 CCCH 3 is oxidised to t-butyl acetate by C 6 H 5 C0 3 H
O
(D) All of the above are correct statements
Q.28 Following equilibrium is favoured in the forward side because of:
R
Y°^C( CH 3) 3 R
Y 0 H +(CH 3 ) 3 COH
o o
(A)(CH 3 ) 3 CO e (alkoxide) - a strong nucleophile is formed
(B) (CH3)3C® (carbocation) is formed
(C) formed is stabilised by resonance

0
Rv. /OH
(D) 11 (a weak acid) is formed
O
Q.29 Column I Column II
(organic compounds oxidised by HI0 4 ) (products of HI 0 4 oxidation)
(A) CH 3 COCHO (P) PhCH = O + HCO OH
(B) 1,2-cyclohexanedione (Q) CH3CH2CHO + HOOCCH 3
(C) PhCH (OH) CHO (R) HOOC (C H 2 ) 4 C00H
(D) CH 3 CH 2 CH (OH) COCH 3 (S) CH 3 COOH + HCOOH
Q.30 Column I Column II

(A) C 6 H 5 - C - OC 2 H 5 + H 3 C - C - 0 - C 2 H 5 -> (P) AnhydrousZnCL
II " II
o o
C 6 H 5 - c - CH 2 - c - O C 2 H 5 + C 2 H 5 O H
II II
0 0
(B) H 3 c - C - OH + Cl 2 C 1 C H 2 - C -O H (Q) C 2 H 5 0,e
o o
(C) C 6 H 6 +(H 3 C-C=0) 2 0 -> C 6 H 5 - C - CH 3 (R) Red P
CH3
ii Ban sal Classes Carboxylic Acids & It's Derivative Aliphatic amines Page # 18
EXERCISE - II
Complete the following equation by writting the missing A, B, C, D. .....etc.
excess
aqKOH
Q.2 Ester (A) — » B +C > (CH 3 ) 2 CHCH 2 QH
H2/Pd BaS04
(D) LiA1H
4 ? (CH 3 ) 2 CHCH 2 OH
„ ND, v Br,,KOH NaN02+HCl • /p\

Q.3 R- CO OH ^ (A) ^ >(B) 2
A A
Mo stAg2
Q.4 A ' °
KCN T j HÔ ?
soci. ^^
Q.5 Acid (A) - >C
E+NaCl
NaOH T g
I C O \
A. PCI, „ MeNH, „
L v> C
Q-6 [ ZCO'
r n > - M ^ -
o
.ci /NH 2 /NH-C-Me
Q.7 O= < + A - ^ O- ^ + B —>0 (unede)
/NHSO3H
c „ o = <
Q.8 CaCN 2 + H O H - i ^ ( A ) - ^ ^ ^ ( B )
(H 2 0 2 )
a
COOH
COOH A > A _A_>B

COOH
•COOH
s
NTOOH A A „
Q.10 •H — A +B
x
COOH
A
Q.ll p h / = ^ . C 0 0 H -» U( )
4 I B a n s a l Classes Carboxylic Acids & It's Derivative Aliphatic amines Page #20
Zn/Hg/HC1
Q.12 PhMe + (A) — p - M e C ^ - C Q - C H ^ a ^ C O O H > (B )
1 0
Q.13 CH 3 (C H 2 ) 14 CH 2 CH 2 COOH > (A) t )^^ " > (B) -J SL ^.
(ii)H'
(i)Ag+(ii)Br
CH 3 (C H 2 ) 14 COOH 2 >( D) -
C H 2 C 0 0 H
Q.14 [ p T C 0 0 H (A) Hd ) (R ) _ic L > f^n Y-^CH.COOH A + C02+H20
COOH
q i 5 +
l i v ;
COOH
O
CI
OH" / a\ OH" . (i )H 2 0
Q.1 6 [ I >(A) >(B)
(II)H30
2Na H / Pd
Q.17 HC=C H ^ > (A ) 2
(ii)2C02 BaS04
A
Q, 18 Phth alica cid + NHL >D >E
Q.19 MeCH(CH2COOH) 2 (CH3CO)2O ) F

A
o H ^ ^ ^
LiA1H4
Q .20 CH 3 -C -N ~( ) > (A)
0 LlA1H
Q.21 [ P l y " ) (B)
Give the mechanism for the reaction with suitable examples:

0
Br /4KOH
Q-22 R-C-NH 2 + 2 " >R-NH 2
0
Q.2 3 R - C - OR' __NaOH_^RCOONa + R'OH
4IBansal Classes Carboxylic Acids & It's Derivative Aliphatic amines Page #21
? RON, A ^
ff
Q.25 R - C - O H + HN3 h
2s°4 >RNH2
o o
II A, CI II
Q.26 R- C- Cl ) R- C - C 6 H 5
O
Q.27 R - C - CI + CFLN2 — > R-CFL-COOH
(ii)H20
Account for following:
Q.28 Fluoro acetic acid is stronger than chloro acetic acid.

Q.29 C-0 bond length in formic acid are 1.23 A and 1.36 A but in sodium formate both carbon and oxygen
bonds have same value i.e. 1.27 A.
Q.30 Acetic acid can be halogenated in presence of phosphorous and chlorine but formic acid cannot be
halogenated in the same way,
Q. 31 The C-G bond in acid derivative is expected to be shorter and stronger than alkyl derivative.
Q. 3 2 An acyl chloride undergoes nucleophilic attack more rapidly than does an alkyl halide.
Q. 33 Primary and secondary amide exist as dimer in solid and pure liquid state.
How will you bring about the following transformation:
Q.34 Propanoic acid into lactic acid.
Q.35 Nitroethane to acetic acid.
Q.3 6 Benzoic acid to benzamide.
Q.3 7 Ethyl benzene to 2-phenyl propionic acid.
Q.38 Acetamide from acetone.
Q.39 Tartartic acid from ethylene.
Q.40 Lactic acid from acetic acid.
Q.41 Pyruvic acidfromethyl bromide.
Q. 42 p-hydroxy propionic acidfromethylene oxide.

1
^Bansal Classes Carboxylic Acids & It's Derivative Aliphatic amines Page # 22
EXERCISE - III
Q. 1 Show by a series of equations how you could synthesize each of the following compounds from the
indicated starting material and any necessary organic or inorganic reagents.
(a) 2-Methylpropanoic acidfromtert-butyl alcohol
(b) 3 -Methylbutanoic acidfromtert-butyl alcohol
(c) 3,3-Dimethylbutanoic acidfromtert-butyl alcohol
(d) H02C(CH2)5C02H from H02C(CH2)3C02H
(e) 3-Phenyl-1-butanol from CH3CHCH2CN
/Br
(f) I A from cyclopentyl bromide
CO2H
rr"
(S) L / LN from (E)-C1CH=CHC02H
Q.2
C02H
On standing in dilute aqueous acid, compound Ais smoothly converted to mevaionolactone.
Me
TRÔ (I)H3Q+ „ O"
I >CH2COOH * I LCH3
Suggest a reasonable mechanism for this reaction. What other organic product is also formed?
Q.3 Suggest reaction conditions suitable for the preparation of compound Afrom 5-hydroxy-2-hexynoic
acid.
CH3CHCH2C = CCO2H — > r v 0
0
OH H,}"
5-Hydroxy-2-hexynoic acid Compound A
Q. 4 Outline reasonable mechanism for each ofthe following reactions
(a) C A + BrMgCH9CH7CH,CH,MgBr —
O O " (ii)H,0
HC xCH2CH2CH2OH
h
n a ya
Q. 5 Identify compounds A through C in the following equations:
O °
(a) C H 3 0 ^ ~ ^ ~ CC1 + CCH — P - ^ U compound A (C22H1804)
OH
fe Bansal Classes Carboxylic Acids & It's Derivative Aliphatic amines Page # 23
o o
(b) CH3CCH2CH2COCH2CH3 - CH3 Mgl (1 equiv) diethyl ether > c o m p ( ) u n d g ( a l a c t o n G ; CÔ,)
o
COH
heat
(c) > compound C (C 9H405) + H 2 0
HOC
0
0
Q.6 An organic compound C4H604 (A) when heated with acetic anhydride give another compound C4H403
(B) which in turn react with ammonia to give a third compound C4H502N (C). Both (B) and (C) may be
hydroiysed to A. With chlorine A give monochloro-compound (D) which reacts with caustic potash to
give either C4H405K2 (E) or C ^ O ^ (F) depending upon the condition of reaction. Identify the
compound A to F.
Q.7 An organic compound A (C4Hc,NO) on treatment with bromine and alkali form another compound B
(C3H9N) on treatment with sodium nitrite and dilute hydrochloric acid. B yield C (C3HgO). C can be
oxidized to D (C3H60). Which can also synthesisedfrommethyl acetylene. Identify the compound Ato D.
Q.8 With bromine and caustic potash the straight chain compound C 4H9ON (A) give C3H9N (B), with
caustic soda C4H702Na (C) and with phosphorous pentoxide gives C4H7N (D). With hydrochloric
acid D give C4H802 (E) ofwhich C is the sodium salt. B may be converted to an alcohol (F) and then to
a halide the grignard reagent from which react with carbon dioxide to give E. On oxidation F give.
Identify the compound Ato H.
Q. 9 Compound (A) with an empirical formula, C7Hc,N on diazotization give a product which undergoes
reaction with Cu2Cl2 & HC1 to give a compound (B). B on oxidation give a compound (C). Compound
(A) on treatment with Br2/H20 form C7H6NBr3 (D). Give the structural formula ofA, B, C & D.
Q.10 An organic compound A (C3H5N) on boiling with alkali give ammonia and sodium slat of an acid B
(C3H602) A on reduction give a compound 0 (C3H9N) which with nitrous acid give D (C3HgO). Give
the structural formula ofA, B, C and D.
Q.ll An organic compound (A) C3H?ON on heating with POCl2 give a compound B which on hydrolysis
give a compound (C) C3H602 with the liberation of ammonia. Compound Aon treatment with LiAlH4
form compound C3H9N (D). Compound D treating with HN0 2 liberate N2 gas on refluxing with
chloroform and alcoholic KOH give compound E which have foul smell. Identify compound A,B, C, D
and E.
Q. 12 An organic compound A (C8HgO) an treatment with NH2OH. HC1 give B and C. Compound B and C
can be converted into D and E respectively by treatment ofH 2S0 4 . Compound B, C, D and E are all
isomer of molecular formula CgF^NO. When D is boiled with KOH, and oil F (C6H7N) separate out.
F react rapidly with CH3COCl to give back (D). On other hand. E on boiling with alkali followed by
acidification give a white solid G (C7H602). Identify Ato G.
Q.13 An organic compound A, (CgH9NO) on heating with conc. H2S0 4 give another isomer of (A) i.e. (B)
C8H9NO. Compound B on hydrolysis with dil HC1 give an aliphatic acid C, C2H402 and (D) on
treatment with NaN02 HC1 at 0°C give a compound (E) which give a white ppt. of AgCl on addition of
AgN03. Compound (E) react with alkaline (3-naphthol to produce orange dye what are to E.
Q.14 An organic compound A of the molecular formula C 4Hg03 give effervescence with sodium bicarbonate
solution and can be acetyl ated. It can be separated into dextro and laevoisomers on heating it forms an
acid B with formula C4H602. Compound B give positive Bayer's test. Identify A and B.
Q.15 An aromatic compound A, CgH5N0 2 can be condensed with an acid derivative (B) C 7 H,,0 4 Br in
presence of alkali to form compound (C), C15H15N0 6. Compound (B) can be prepared by action of
sodium followed by bromine gas on diethyl malonate. Compound (C) condensed again with ethyl chloro
acetate in presence of sodium to give compound (D) C 19H21N0 8. D on heating with a base can be
converted into E and a salt of acid F (CgH604). Compound A can be obtained by heating F with
ammonia. E on boiling with mineral acid produce amino acid G (C4H7N04). Identify Ato C.
Q.16 An organic acid A(C3H40 3) is catalytically reduced in presence of ammonia to give (B) C3H7N02. B
react with acetyl chloride hydrochloric acid and alcohol. It can also react with nitrous acid to give
another compound (C) C3H60 3 along with evolution of N2. What are (A), (B) and (C)?
Q.17 A dibasic acid (A), C4H606, on heating with KHS0 4 give a monobasic acid (B), C3H403, with the
elimination of C0 2 and H2 0. Acid (B) on reduction give another monobasic acid (C), C3H603. Both
(B) and (C) on heating with I2 and NaOH solution give yellow precipitate of iodoform and sodium
oxalate. Acid (A) react with two moles of acetyl chloride, while (C) reacts with one mole of acetyl
chloride. Acid (A) reacts with four moles of HI to form succinic acid, while (C) react with two moles of
HI to give propionic acid. Identify A, B, C and give equation for reaction.
Q.18 An organic compound of the formula C3H60 (A) gave iodoform test but not Tollen's and Fehling tests.
Two molecules of (A) condenes in presence of dry HCl gas to yield (B) of formula C6H10O. Compound
(B) decolourised Br2/CCl4 and cold dilute neutral KMn0 4, but no ppt. with ammonical AgN0 3 or
CuCl solution. It gave iodoform test and potassium salt of a compound on heating with I2 and KOH. The
potassium salt on treatment with H 2 S0 4 gave compound (C) of formula C5H80 2. Compound (C) on
heating with sodalime gave (D) of formula C4Hg. Identify compound Ato D & write the chemical
equation.
Q.19 An organic compound (A) of formula C3H6Qfroma monoxime with hydroxylamine and form iodoform
on heating with I2 and NaOH and sodium acetate. Compound A on reaction with NaCN and dil. H2S04
gave product B. Which on hydrolysis produced (C). Compound (C) on heating gave (D), which on
decarboxylation gave (E) of formula C3H6. Compound (E) on ozonolysis gave one molecule of
acetaldehyde and one of methanal. What are Ato E?
Q.20 Two moles of an ester (A) are condensed in the presence of sodium ethoxide to give a P-keto ester (B)
and ethanol. On heating in an acidic solution (B) gives ethanol and J3-keto acid (C). On decarboxylation
(C) gives 3 -pentanone. Identify (A), (B) and (C) with proper reasoning. Name the reaction involved in
the conversion of (A) to (B).
Q.21 An acidic compound (A), C4Hg0 3 loses its optical activity on strong heating yielding (B), C4H60 2
which reacts readily with KMn04. (B) forms a derivatives (C) with SOCl2, which on reaction with
(CH3)2 NH gives (D). The compound (A) on oxidation with dilute chromic acid gives an unstable
compound (E) which decarboxylates readily to gi ve (F), C3H60. The compound (F) gives a hydrocarbon
(G) on treatment with amalgamated Zn and HCl. Give structures of (A) to (G) with proper reasoning.
Q. 22 An organic compound (A), C5H803 on heating with soda-lime gives (B),which reacts with HCN to give
(C). The compound (C) reacts with thionylchloride to produce (D), which on reaction with KCN gives
compound (E). Alkaline hydrolysis of (E) gives a salt (F), which on heating with soda-lime
produces -butane. Careful oxidation of (A) with dichromate gives acetic and malonic acid. Give structures
of (A) to (F) with proper reasoning.
Q.23 An acid (A), C gH ?0 2 Br on bromination in the presence of FeBr gives two isomers, (B) and (C) of
formula CgH602Br2. Vigorous oxidation of (A), (B) and (C) gives acids (D), (E) and (F) respectively.
(D), C7H502Br is the strongest acid among all of its isomers, whereas (E) and (F) each has a molecular
formula of C7H402Br2, Give structures of (A) to (F) with justification.
EXERCISE - IV (A)
O
Q.l The reaction of R -C -N H 2 with a mixture of Br2 and KOH gives R-NH2 as a product. The
intermediates involved in this reaction are: [BIT 1992]
? II
(A) R- C- NH Br (B)R-N=C=0 (C)R-NHBr (D)R-C-N<
Br
Q.2 Which ofthe following carboxylic acids undergo decarboxylation easily: [IIT 1995]
(A) C6H5CO-CH2COOH (B) C6H5COCOOH
(C) C6H5CH 2-COOH (D) C6H5CH2 - COOH
I .1
OH NH2
Q. 3 The molecular weight of benzoic acid in benzene as determined by depression infreezingpoint method
corresponds to : [IIT 1996]
(A) Ionization of benzoic acid (B) Dimerisation of benzoic acid
(C) Trimerisation of benzoic acid (D) Solvation of benzoic acid
Q.4 When propionic acid is treated with aqueous NaHC03, C0 2 is liberated. The 'C' of C0 2 comes from
(A) Methyl group (B) Carboxylic acid group
(C) methylene group (D) bicarbonate [IIT1999]
Q.5 Benzoyl chloride is preparedfrombenzoic acid by: [IIT 2000]

(A) Cl2, hv (B)S02C12 (C)SOCl2 ( D^H JO
Q. 6 Which of the following acids has the smallest dissociation constant? [Ill 2002]
(A) CHXHFCOOH (B) FCH2CH2COQH (C) BrCH2CH2COOH(D) CH3CHBrCOOH
ÔCQCH3
v
P Acidic v
Q.7 Hydrolysis ProductsformedbyP&Q can be differentiated by [IIT2003]
(A) 2 & 4 DNP (B) Lucas reagent (ZnCl2)conc. HC1

(C)NaHS03 (D)Fehlings solution
Q.8 Whenbenzamid is treated withPOCl3, the product is: [IIT 2004]

(A) Benzonitrile (B) Aniline (C) Chlorobenzene (D) Benzylamine
Q. 9 Which of the following is obtained when 4-Methylbenzenesulphonic acid is hydrolysed with excess of
sodium acetate? [IIT 2005]
( A ) C H 3 -< fy -C OO Na (B) CH3 7 + S0 3
(C) CH3 ~ f V s oS0r 3NNa

a +
+CHXOOH
CHgCOOH CH,3
(D) CH ^\- S 0 2 0 . COCH3 + NaOH
Q.10 The correct IUPAC name of C6H5G0C1 is

(A) Benzoyl chloride (B) Benzene chloro ketone
(C) Benzene carbonyl chloride (D) Chloro phenyl ketone [IIT 2006]
Q.ll Which ofthe following reactants on reaction with conc. NaOH followed by acidification gives the followin
lactone as the only product? [IIT 2006]
O
\>
/
CH 7
COOCH3 COOH COOH

b
<»a COOH <>OC \ CHO « c c »cc COOH
EXERCISE - IV (B)
Q.l Compound (A) (C6H1202) on reduction with LiAlH4 yielded two compounds (B) and (C). The compound
(B) on oxidation gave (D) which on treatment with aqueous alkali and subsequent heating furnished (E)
The latter on catalytic hydrogenation gave (C). The compound (D) was oxidised further to give (F)
which was found to be monobasic acid (molecular mass = 60.0). Deduce the structure of (A), (B), (C),
(D)and(E). [IIT 1990]
Q.2 In the following reactions, identify the compounds (A), (B), (C) and (D) [IIT 1994]
PC15 + S0 2 —->(A) + (B)
(A) + CH3COOH > (C) + S0 2 + HCl
2(C) +b (CHACd - 2(D) + CdCL
Q.3 Complete the following equations by writing the missing A and B [IIT 1995]
;f2 (A) (i)Alc.KOH(excess) (g)
(i) CH,CH,COOH > )
(ii)H
(ii) C4H„03(A) (B)
Q.4 A mixture of an acid anhydride (A) and a monobasic acid (B) on heating produces another monobasic
acid (C) of equivalent weight 74 and an anhydride (D). The acids and anhydrides remain in equilibrium
The anhydride (D) contains two identicalfluoro-alkylgroups. The acid (B) contains a trifluoromethyl
group and has an equivalent weight of 128. Give structures of (A) to (D) with proper reasoning. (Atomic
weight offluorine =19). [HT 1998]
Q.5 Identify Aand B in the following equations: [IIT 1999]
H3C^^cooc2H5
o
CH
(i)OH~
.(A)" .(B)
\COC2H5 (ii)H + A
0 CH--C-OH
2
II
o
Q.6 Write the structure of product A&B: [IIT 2000]

O
CH3-C-O18C2H5 H3 +
° >A+B
Q. 7 Identify X, Y and Z in the following synthetic scheme and write their structure. Explain the formation of
labelled formaldehyde (H2 C*0) as one of the products when compound Z is treated with HBr and
BaC*0 3 +H 2 S0 4 >C (gas) [C* denotes C14] [IIT 2001]
( )Mg/ether
CH22 = CH - Br '
(II)X
(iii)H30+
Q. 8 Mention two esters pro duced when a racemic mixture of 2-phenyl prop anoic acid is treated with (+)
2-butanol. What is the stereochemical relationship between these esters? [IIT 2003]
Q.9 Give major products A, B, C and D in following reaction sequence. [IIT 2004]
C H 2 -C1
KC N V A (i)NaOEt/EtOH v H, 0® „
f /—-N 1 >n
( ) DMF (ii)P hCHO/ A
socl 2
n
(ii) CH 3 NH 2
ANSWER KEY
EXERCISE -1(A)
Q.l C Q.2 B Q.3 C Q.4 B Q5 C Q.6 A Q.7 A

Q.8 D Q.9 C Q.10 c Q.ll C Q.12 B Q.13 C Q.14 C
Q. 15 A Q.16 D Q.17 B Q.18 C Q.19 A Q.20 A Q.21 A
Q.22 B Q.23 B Q.24 A Q.25 A Q.26 A Q.27 A Q.28 B
Q.29 D Q.30 C Q.31 A Q.32 C Q.33 A Q.34 B Q.35 D
Q.36 B Q.37 B Q.38 A Q.39 A Q.40 B Q.41 B Q.42 C
Q.43 A Q.44 A Q.45 A Q.46 D Q.47 C Q.48 B Q.49 C
Q.50 C Q.5I B Q.52 B Q.53 D Q.54 C Q.55 A Q.56 C
Q.57 A Q.58 D Q.59 C Q.60 C Q.61 D Q.62 C Q.63 A
Q.64 A Q.65 B Q.66 B Q.67 B Q.68 C Q.69 D Q.70 C
Q.71 D Q.72 C Q.73 A Q.74 C Q.75 A Q.76 C Q.77 A
Q.78 C Q.79 C Q.80 C
EXERCISE - KB)
Q.l A,B,C Q.2 B,C Q3 A,B,C,D Q.4 A,B
Q.5 A,B,C Q.6 A,C Q7 A,C,D Q.8 A,B,C,D
Q.9 A,B,C,D Q.10 A,B,C Q.ll A,B Q.12 A,B
Q.13 B,C Q.14 B,C Q.15 A,B,C,D Q.16 B
Q.17 A,B,C Q.18 A,B,D Q.19 A,B,C,D Q.20 A,B,C,D
Q.21 A,B,C Q.22 D Q.23 A,B,C Q.24 A,B
Q.25 A,B,C Q.26 B Q.27 D Q.28 B
Q.29 (A)S,(B)R,(C)P,(D)Q
Q.30 (A)Q, (B)R ,(C )P,(D )S Q.31 (A) R, (B) P, (C) S, (D) Q
Q.32 (A)Q,(B) S, (C)P,(D)Q Q.33 (A) S, (B) Q, (C) P, (D) R
Q.34 (A)S,(B)Q,(C)S,(D)R Q.35 (A) P, (B) R, (C) P,S, (D) Q
EXERCISE - II
Q.l (A) CH3CH(OOCCH3)2; (B) CH3CHO; (C) (CH 3 C0 ) 2 0
Q.2 (A) (CH3)2CHCOOCH2CH(CH3)2 ; (B) (CH3)2CHC0C1; (C) (CH3)2CHCH2C1
Q.3 (A) RCOND2; (B) RNH2 ; (C) ROH
Q.4 (A) CHgCl; (B) CH3OH; (C) HCOOH; (D) Ca(OH) 2; (G) HCHO; (H) CH3C1; (I) KCN; (J) CH3CN;
(X)CH3 COOH
Q.5 (A) CH3COOH; (B) CH3COONa; (C) CH3COCl; (E) (CH 3 C0 ) 2 0
Q.6 (A) HOOCCH 2CH2COOMe; (B) C10CCH 2 CH 2 C00Me; (C) MeNH0CCH 2 CH 2 C00Me
Q.7 (A) 2NH3; (B) CH3COCl; (C) H 2 S0 4 + S0 3
O
^NH-
CH-,
Q.8 (A) HjNCONH^; (B) O \ Q.9 (A )k 1 ;( B) [ T
NH" "C
ft
rooH
S
o Ph-
H II
Q. 10(A) M (B) Q 11 (A) .00
[
COOH
-C"
II
o
Q.12 (A) 'o; (B) p-MeCg^CKLjCHjCHjCOOH
Q.13 (A) CH 3 (C H 2 ) ]4 CH 2 CHBrCOOH; (B) CH 3 (C H 2 ) 14 CH=CHCOOH; (C) KMn0 4 ;

(D)CH 3 (C H 2 ) 14 Br
Q14 (A CN o t (D) 1:c=o

> tOXc„,oH ; (B
> ^lcH2cr(C) ^ - tOD
H
COOH
COOH
Q.l 5(A) 1 0 0H ;(B) L°° H
Q.16 (A) ;(C)
H
COOH COOH
Q.17 (A) C CO OH; (B) H-C-COOH; (C) ( D) C 0

H COOH' H V
H-C-COOH N^T+COOH
X T H -CO^
C COOH ^ H
^ H
S Me
ON H 4
Q.18 (D)[0 N- H Q.19 (F) H'
-ONH4 ;(E) O y
CH 2OH
Q.20 (A)CH 3 CH2NH- Q.21
CH 2 OH
EXERCISE - III
CH 2 COOH C H 2 CO\ C H 7 CO\ CH 2 CICOOH
Q.6 (A) (B) (C) ! > H (D)
C H 2 C O /p
CH 2 COOH C H 2 CO/ I 2 COOH
CH
Succinic acid Succinimide
Succinic anhydride
CHCOOK
CH 2 (OH)COOK
(E) (F)
CH 2 COOK CHCOOK
Potassium maleate
Q.7 (A) (CH 3 ) 2 CHCONH 2 ; (B) (CH 3 ) 2 CHNH 2 ; (C) (CH 3 ) 2 CHOH; (D) CH 3 COCH 3
Q.8 (A) CH,C H 2 CH 3 C0NH 2 ; (B) CH 3 CH 2 CH 2 NH 2 ; (C) C^C^CH^COONa; (D) CH 3 CH 2 CH 2 CN

(E) CH 3 CH 2 CH 2 COOH; (F) CH^ CHj CI^ OH ; (G) CH 3 CH 2 CHO; (H) CT^CH^COOH
NH 2 CI CI
Q.9 ( A
) f O L „ (B)fOl„„ .(C) [ O
CH, •CH, COOH
Q.10 (A) CH 3 CH 2 CN ; (B) CH 3 CH 2 COOH; (C) CH 3 CH 2 CH 2 NH 2 ; (D) CH^CHjCHJOH

Q. 11 (A) CH 3 CH 2 CONH 2 ; (B) C 2 H s CN; (C) C 2 H 5 COOH; (D) C ^ C H ^ ^ N F ^ ;
© ©
, (E)CH 3 CH 2 CH 2 N = C
0 CH, CH3OH O
C-CH 3 ; ( B ) r f ^ r C = N - O H c)r ^[- C= N |f>r NH- C-C H
Q.12 (A) ;( ;(D)
0
C-NH-CH, II
(E) (G) C-O H
CH3 o
II
Q.13 (A)^Q C = N -OH ;(B) N H - C - C H 3 ; (C) CH3COOH;
N
2Cr
(E)FO
OH
Q.14 (A) CH3 - CH - CH 2 - COOH; (B) CH3-CH=CH-COOH
\
Q 15 (A) N_H; (B) Br-CH(COOEt)2; (C) ^N-CH(COOEt)2 ;
COOEt
COOEt
C-OH
-CCH X O O Et. (E) H 2 N-CCH 2 COOEt; (F) C-OH
COOEt <i 00Et 0
Q.16 (A) CHJ = C(OH)-COOH; (B) CH^CCNH^-COOH; (C) CH3CH(OH)-COOH
CH(OH)COOH
Q.17 (A) ] ; (B) CH 3-CO-COOH; (C) CH,-CH(OH)-COOH
CH(OH)COOH
Q.18 (A) CH3-CO-CH3; (B) (CH3)2C=CHCOCH3; (C) (CH3)2C=CHCOOH; (D) (CH3)2C=CH2
Q.19 (A)CH3-CO-CH 3; (B) (CH3)2C(OH)CN; (C) (CH3)2C(OH)COOH; (D) CH2= C-(CH3 )-COOH
(E) CH3-CH=CH2
Q.20 Claisen condensation, (A) C2H5COOC2H5; (B) C2H5COCH(CH3)COOC2H5;
(C) C2H5COCH(H3)COOH
Q.21 (A) CH3CH(OH)CH2COOH; (B) CH3CH=CHCOOH; (C) CH3CH=CHCOCl
(D) CH3-CH=CHCON(CH3)2; (E) C^COCH^COOH; (F) CH3COCH3; (G) CH3CH2CH3
Q.22 (A) CH 3-CO-CH 2CH 2 -COOH; (B) CHgCOCK^CT^; (C) CH3C(OH)(CN)CH2CH3
(D) CH3C(C1)(CN)CH2CH3; (E) CH3C(CN)2CH2CH3; (F) CH3C(COONa)2CFL,CH3
f V V r C H 2 COOH (7-Op CH 2 C O O H 2r n O H iV ^V CO OH
Q.23 (A) [ O I RBrr 2 ; (B) B r j O J - B r i (9 f O
Y
° ° ' (D)[UJ-Br
-Br
-COOH
O -Br
(E) (F ) lOjBr
Br
EXERCISE - IV (A)
Q. l A,B Q.2 A Q.3 B Q.4 D Q.5 C Q.6 C Q.7 D
Q.8 A Q.9 C
EXERCISE - IV (B)
Q. 1 (A) C H ^ C f ^ C O O C f ^ C H , ; (B) C H3 CH 2 QH; (C) CH 3 CH 2 CH 2 CH 2 OH; (D) CH 3 CHO;

(E) CH 3 CH= CHCHO
Q.2 (A) S0C1 2; (B) P0C1 3 ; (C) CH 3 C0C1; (D) CH 3 COCH 3
Q.3 (i) (A) CH 3 CHBrCOOH; (B) CH 2 = CHCOOH;
(ii) (A) CH 3 CH(OH)CH2COOH; (B) CHjCOCF^COOH
Q.4 (A) (C H 3 CH 3 C0) 2 0; (B) CF 3 CH 2 COOH; (C) CH 3 CH 2 COOH; (D) ( C F ^ C O ^ O
HC-(COOC2H5)2
Q. 5 (A) NaCH(COC 2 H 5 ) 2 ; (B) CH 3 - HC - COO C 2 H 5

Q.6 (A) CH 3 COOH; (B) C 2 H s 0 1 8 H
Q.7 BaC*0 3 + H 2 S 0 4 > C*0 2 (X) + BaS0 4
(i)Mg, (ii)C*Q 2
CH 2 =CH-B r — ^
( i i i ) H3 0 +
CH 2 =CH-C*OOH(Y) LiA1H
4 >
H+
CH 2 =CHC*H 2 OH(Z) >
CH 2 =H-C * H J < > C* H 2 CH=C*H 2

I Br iBr
CH 2 =CH-C*H 2 Br BrCH2 - C H ^ C * ^
I 0 3 ZNH 2 0 I O ^ n f ^ O B r- C* H2 CHO + HCHO Br- CH 2 CHO + HC*HO
Ph H ' (+) CH3 CH 2 -C-OH
Q.8 CH 3 - CI - C O O H + C H 3 - CI- C O O H ICH,

| ~ | con c.H 2 S0 4 , A
H Ph
(racemic mixture)
Ph H H H
I I I I
CH3-C-C-0-C-CH2CH3 + CH3-C-C-O-C-CH2CH3
' ! I I ' I II I
H 0 CH 3 Ph O CH 3
during esterification reaction only - C OO H and - O H partcipates. There is no effect on structure or

configuration of carbon adjacen t to these groups. So when(± ) acid reacts with pure (+) alcohol two
esters are produced which are diastereoisomers of each other.
CN COOH CONHCH3
9VCN CH=CÔ) CH=C-(p) CH = C
Q.9 <A)(g) ( B ) ^ (O fg s ^ ( D ) ^ ^ ,
ORGANIC CHEMISTRY
XII (ALL)
CONTENTS
EXERCISE-I
EXERCISE-II
EXERCISE-III
EXERCISE IV
ANSWER KEY
EXERCISE-I
(Choose the correct option. Only one is correct)
H >
Q.l I X° — A, the product A is:
(A> m (
\/\/ Q A C , < X > „ c d
„ <$2 Which carbocation is least likely to form as intermediate?
( C )
(A)(C6H5) 5C ( B ) Q e Cf) (D) CH 2 =CH
sj^. 3 2-chloropentane on halogenation with chlorine gives 2,3, dichloropentane. What will be the structure of
free radical species form in the reaction?
(A) Planar (B) Trigonal planar (C) Square planar (D) Pyramidal
What will be maj or product, when 2-methyl butane undergoes bromination in presence of light?
(A) 1 -bromo-2-methyl butane (B) 2-bromo-2-methyl butane
(C) 2-bromo-3-methyl butane (D) 1 -bromo-3-methyl butane
The smallest compound, which on photochlorination produces diastereomers is
(A) 3-methyl, 3-chloro hexane (B) 2-chloro butane
(C) 1 -bromo propane (D) 1 -bromo-3-methyl butane
Q.6 Which of the following will give two isomeric monochloro derivatives?
(A)2,3-dimethylbutane(B)n-hexane (C) Isopentane (D) Butane
Q.7 How many isomers can be producedfromthe molecular formula C4H10O?
(A) 8 (B)7 (C)6 (D)5
Et > 1116 ma or ro duct i s
Q. 8 ° ~ J P
Cl-v Cl-\ EtO

OEt
(A) ) t (B) ) t (C) [\* (D)
HO OEt EtO OH ° O
Ph
J
^ & L>CH3
CT
3
H3 O
+
>?
Phv. Ph\ Ph^
(A) | (B) I (C) | (D) None of these
HOA^CHS HO^YCHA R A ^
R OH OH
Halogen Derivatives
^Bansal Classes [2]
* /^v-OH
^071 0 I J P. The product Pis:
^ OH
(A) | (B) (C) (D)
Among the given compounds, the correct dehydration order is:
a ) O O H ( i i ) P O (iv)
(A) I < I I < I I I < I V (B) II < III < IV < I (C) I < III < IV < II (D) I < II < III = IV
Q.12 Identify Z in the following series of reaction:
Q H c o n c. H 2 SQ 4 ) X Br , > y alc.KOH > z
a
170 C CC1- A
CH,
H,C-
3
(A) ( B ) H 3 C - ^ ( C ) H 3 C — ^ ( D ) H 3 C - ^
HO OH CH CH 2
Q.13 In the reaction sequence

OH O
( i ) N a0Br
C6H5- CH- CH2- C- CH3 >product
(ii)H20/H+
(iii)A
product will be
OH
(A) C 6 H 5 - CH - CH 2 - COOH (B) C6H5-COOH, COOH-COOH and CHBr3

O
II
(C) C 6 H 5 - C - CH 3 , C0 2 and CHBr3 (D) Only CHBr3
, C1F 2 C X / F
c =C leg. -QEt ) A (major product). A is

tt/ \
OEt
C1F2CX .OEt CIF2CV / F I C1F 2 C X / F
F
(A) Ph/ = C F (B) PhJX> C OEt (C) pPhh > - 9 I- (D) OEt > <X F
F
CH s H+
(l5 J |\:H 3 > major product is
O ^ S . C H CH3 CH3 CH3
(A) 0 H
k X „ ! w (C) (D) ^ A x C H 3
Halogen Derivatives
faB an sa l Classes [3]
Q/T6 HBr reacts fastest with

^ (A) 2-methyl butane-2-ol (B) 3 -methyl butane-2-ol
(C) Butane-1 -ol (D) 2-methyl butane-1 -ol
,COCH3
Q.17
- e[ x NaOBr ) Product
The product is
« o <»oc « o c ~ » o £ .
CH,
nu
/OH /OH
(A) V J—CH- <&< I ( O /OH~\

TA „
^ (D)
OH 'OH
J?.f9 Which one of the following alcohol will undergo acid catalysed dehydration with greatest ease by E,
mechanism?
(A)CH2 = CH-OH (B)!"] (C) (D)Me2CHOH
T OH
OH
NaCN
0C2O (A) C3 H60 H 2 SO 4 > cyanohydrin of (A). If the cyanohydrin is optically active, then the possible
structure of (A) is
(A) ( B ) ^ (C )P >- OH (D) | ]
. 1 Which ofthe following has minimum reactivity towards nucleophiles?

O O
II II
(A) CH20 (B) CH3CHO (C) CH3 - c - CH3 (D) CH3 - c - CH 2 - CH3
+
X I LL RO H/ H V
sj^.22 J) » P (major org. product)
The product Pis
(q ( d )
- a QH3 0
OR
Halogen Derivatives
^Bansal Classes [4]
Q.23 C1 3 £-CH = CH2 H3C—CH=CH2
(I) (II)
In addition of HOBr to (I) and (II)
(A) Br is at C2 in both cases (B) Br is at C2 in II and at C, in I
(C) Br is at C, in II and C2 in I (D) Br is at C j in both cases
4 Greatest amount ofhydration is in
(A)[^| m ( y (C) [ ^ B r " (D) All are equal
Q.25 \ f 1 e qu iv alen t M g > X — > Y ; Y is

ether
^ ^Br
(A)\ J ( B) \ J (C)\ J (D) none of these
How many number of optically active isomers are possible for 2,3-dibromo butane 1,4-dioic acid?
(A) 2 (B) 3 (C)4 (D)l
~<K Q-27 y—N— and \ n-^
Are which type of isomers

(A) Chain (B) Position (C) Metamerism (D) functional
Most stable conformation of ethylene glycol

(A) Eclipsed form (B) Staggered form (C) Skew form (D) None of these
Which has maximum B.P.?
H 3C .CH,
H 3C CH3
^ H ^ C / ^ ^ ^ v / 0 1 1 3 B).
H3CV H3CV ^ .C H,
(C)H 3 c^/CH 3 (D)

H3C H
x &30 Which of the following carbocation is most stable? (/CazI V
CH3 CH3
(A) A S ™ (B) / V C H 3
H3C H3c OH
CH, CH,
0 3
(C) /K/ ** (D) OH
V
HO CH
faBansal Classes Halogen Derivatives [5]
1 Which of the following alcohol shows fastest reaction with HI ?

OH
(A) ( B )
A A
'OH
H (D)
( O h , C ^ ° I
2 Which ofthe following is strongest base. <
C H (
C H 3 ^ N ^ C H 3 CH3S N /CH3 CH3X N / CH 3 3 \ N /
(a)
fo) <b) f o J C H 3 (c)
( o ) (D )
[ o
CH3
3 In which ofthe following molecule all the effect namely inductive, mesomeric & hyperconjugation operate
C H
( A ) < ^ - C 1 ( B ) \ _ / " 3 ( C ) ( > C O C H 3 (D)<
CH3 CH,
For the reactions
(I) O * + C l e , AH°
(II) O c , > + Cl° , AH°
(III) ^)-CH2CL > ^- CH 2 + CI, AH 3
(IV) { > C 1 > { ^ y ® + CI® , AH°
The correct decreasing order of enthalpies ofreaction for producing carbocation is

(A) AH° > AH° > AH° > AH° (B) AH° > AH° > AH° > AH°
(C) AH° > AHj > AH° > AH° (D) AH° > AH° > AH° > AH°
Jtr
Correct order of basicity of various nitrogen in LSD is
(A)1>2>3 (B)2>1>3 (C) 2>3>1 (D)3>2>1
Halogen Derivatives
faBansal Classes
[6]
Q.36 One of the configuration of n-butane is drawn in the given figure. Anticlockwise rotation of C2 around
C 7 -C , bond by 120° will lead to
CH3
M
(A) gauche (B) staggerred (C) partially eclipsed (D) fully eclipsed
Which of following is correctly matched.
OH
(A) CH3 - C - CH 3 , E, reaction (B) CH 3 -CH 2-CH 2OH, E,cb reaction
I
CH3
OH
I
(C) CH3 - C - CH 3 , thermal reaction (D) CH 3 -CH 2 -CH2~N-Cr , E t cb reaction
I
CH \ C H 33
3
8 Arrange reactivity ofgiven alcohol in increasing order of elimination reaction

(I) CH2 - CH2 - CH2 - CH2OH (II) CH3 - CH2 - CH - CH2OH
I I
NO2 NO2
(III) CH3 - CH - CH 2 - CH 2OH (IV) CH 3 -CH 2 -CH 2 -CH 2 OH

I
NO 2
Select answerfromcodes given below:

(A) I, II, IV, III (B) I, II, III, IV (C) II, III, I , IV (D) II, III, IV, I
t- p.
Arrange leaving power ofNu group in decreasing order
O
eff © ©
(I) o-S-C 6 H 4 - C H 3 (II) O-S-C 6 H 5 (III) N 3 (IV) Br
O O
(A) II, I, III, IV (B) II, I, IV, III (C) I, II, IV, III (D) I, II, III, IV
^J^/40 Arrange decreasing order ofreactivity ofthese compounds for nucleophilic substitution reaction
O
II
(I) CH3 - CH 2 - O - S - CF3 (II) CH 3 -CH 2 -0-TsCl
(III) CH3 - CH - CH 3 (IV) CH3 - CH - OH
OH C6H5
(A) III, IV, I, II (B) III, IV, II, I (C) I, II, III, IV (D) I, II, IV, III
tBansal Classes GOC [7]
X^41 X 3 < H
H 3 + O H
^ A
' A i S
HOv / \ 7CH3 H\ / \ /CH 3

(A) H X^_y\H (B) ^ (C) Both are correct (D) None is correct
Ph
CH3
Q.42 alc.KOH A, A is
CI.
Ph
ch3^C6H5 CH3\ /C6H5
(A) • » (B) (C) (D) None is correct

H ^C6H5 C6H5- CfiH< ^C6H5
Q.43 Major product obtained in reaction of 1 -phenyl-2-bromo butane with NaOMe.

(A) (E)-l-phenyl but-l-ene (B) (E)-l-phenyl but-2-ene
(C) 1 -phenyl-1 -ethoxy butane (D) (Z)-1 -phenyl but-2-ene
Q.44 2-Aminocyclohexane-1 -ol on treatment with HN0 2 produces
(A) Cyclopentane carboxaldehyde (B) Cyclo hexane-1,2-diol
(C) 2-amino cyclohexene (D) Cyclohex-2-enol
5 Arrange the following in order of C-Br bond strength in polar solvent.
®o<i ® o c ®Oc. <-Qc

(A) I < II < III < IV (B) III < IV < I < II (C) I V < II I < II < I (D) II < I < III < IV
46 CI EtOH OEt RateR

s /
3 EtOH Rate R2
EtOH ——R -OEt RateR3

>
v
vX5
Which of following is correct:
( A ) R , > R2 > R 3 (B)R3>R2>R! (C )R 2 > R , > R 3 (D )R 2 > R 3 >R J

Among the foloowing pairs in which case the second compound has higher heat of hydrogenation.
(A) | || , [ f ^ ] (B) Cis-2-butene,trans-2-butene
(C) (D) 1-butene, 2-butene
Q A ^ (I) which is not correct about (I)
(A) I is more soluble than bromocyclopropane

(B) I gives pale yellow ppt. on addition with AgN03
(C) I is having lower dipole moment than bromocyclo propane
/ -B r
(D) I have more ionic character than
Q.49 \^ T C ( C H 3 ) 3 + CH3SNa C
^0H > ?
The product formed is

(A) CH33SCH,2 -C H-C (CH 33) 33 (B) (CH 3 ) 3 C-CH-CH 2 OH
(
OH SCH3
(C) CH3SCH2CH-C(CH3)3 (D) (CH 3 ) 3C-CH2 CH~SCH3
OH OH
Q.50
Correct order of basicity is

(A)3>1>2>4 (B)3<1<2<4 (C)3<4<1<2 (D)3>4>1>2
a 1 Which of the following statement about the reactivity of 1 -chloro apocamphane y

toward AgN0 3 is true. J
(A) React by SN1 mechanism (B) React by SN2 mechanism f"
(C) React by SNi mechanism (D) Does not react ^ci ^
Q.5 2 The resonance energy of following heterocycles is in the order

(A) pyrole > furan > pyridine (B) furan > pyrole > pyridine y? ^ ^ ^
(C) pyridine > pyrole > furan (D) pyridine > furan > pyrole
Arrange the following halide in decreasing order of SN1 reactivity.

(I)CH3CH2CH2a ( „)CH 2 =CHCHCH 3 ( „ I ) C H 3 C„ 2 C„CH 3
CI CI
(A) I > II > III (B) II > I > III (C> II > III > I (D) III > II > I
^Bansal Classes Halogen Derivatives [9]
EXERCISE-II
(iChoose the correct option. One or more than one are correct)
/f
O.l \ = / which is/are incorrect statements?
v
P Q
(A) P is cis- and Q is trans- (B )P i sZ a nd Q is E
(C) P is R and Q is S (D) P and Q are having same structural formula
Q.2 CH 3CH 2 N0 2 will not show. isomerism:
(A) Chain (B) functional (C) tautomerism (D) geometrical
CHCOOH
Q.3 (maleic acid) can form:
CHCOOH
(A) stereoisomer (B) geometrical isomer (C) position isomer (D) functional isomer
Q.4 Which can show tautomerism ?
(A) (B)Ph-CH 2 -NO (C) CH 3 ( D) C H3 -C-NH,
m - o
CH 3 CH 3 H
Q.5 A A
V \ /
CH 3 H H CH 3
I II
I and II are not
(A) achiral-identical mirror images (B) chiral-enantiomers
(C) geometrical isomers of each other (D) racemic mixture
Q.6 In which offollowing compound chiral center is not affected on heating.

(A) CH, - CH - COOH (B) ( \=0
S
PCH
CH 3
OH HOOC
(C) CH 3 - CH - CH 2 - COOH (D) CH 3 -CHCOOH
OH CH 2 COOH
Q.7 Which are correct statements?

(A) methyl malonic acid is converted into propanoic acid on heating
(B) succinic acid forms succinic anhydride on heating
(C) 3-hydroxy propanoic acid forms Lactide on heating
O
(D) CH 3 - C - CH 2 COOH forms acetone on heating
Q.8 Select incorrect statements:
(A) ( 5 > 0 H and yÔH both give colour with neutral FeCl3 solution
(B) 2-pentanone and 3-pentanone are metamers
(C) product formed when benzaldehyde reacts with hydroxylamine shows optical isomerism
(D) 1,2-dibromocyclohexane shows geometrical and optical isomerism.
Sodahme
Q.9 C 5Hg0 4 (A) C 4 H 8 0 2 (B) > (C)
A
C is hydrocarbon occupying 0.509 litre per g approximately. Hence A and B are:
(A) methyl malonic acid, propanoic acid (B) succinic acid, succinic anhydride
(C) Dimethylmalonic acid, 2-Methylpropanoic acid (D) Ethyl Malonic acid, Butanoic acid
O
II
o—c
Q-io ch 3 -o^^CH-CH 3 h3°+ >
products can be: (Both stable & unstable form)

(A) CH3CH(OH)2, CH3CH(OH)COOH (B) CH3CHO, CH3CH(OH)COOH
(C) CH3CH2COOH, CH3CH2OH (D) CH3CH(OH)COOH, CH3CH2OH
Q.ll Which are incorrect statements:
(A) ^ ^ = 0 and 0=^ ) are enantiomers
O O .
CI CH3
I I
(B) CH, - C - CHXH, and CI - C - H are enantiomers
3 2 3 |
H CH2CH3
(C) Argol (sodium potassium tartarate) will show optical isomerism.
(D) CH3CHO on reaction with HCN gives racemic mixture.
Q.12 Which is/are less acidic than Benzoic acid?
(A)CH3COOH (B)(0)"cooh (C)\O/-C00H (D)H 2 0
3 NO2
Q.13 Which have active methylene group?
(A) CH3 - C - CH2 - C - CH3 (B) CH3-CH2-NO2
o O 0
(C) C H 3 - C - C H 2 - C - 0 - E t ( O V
Q.14 Which of the following are not resonating structures of each other:
Q.15 The unshared electron on the oxygen atom of an ether (basic centre) account for all the following except:
F
C2H5N. |
(A) Combination > 6= » B- F
c,H 5
F
/ cr
(B) Formation of oxonium salt with acids such as
(C) Formation of peroxides (explosive)

(D) Chemical inactivity of ether
Q.16 Which ofthe following compounds yield most stable carbanion after rupture of(CJ-C2) bond:
0 0 O
II II II
(A) CH3 - C - CC13 (B) CH3 - C - CBr3 (C) CH3 - CH2 - C - CI3 (D) none of these
1 2 1 2 1 2
Q.17
N
I
H
pyrrole (I) pyridine (II) aniline (III)
which is/are correct statements ?
(A) I is more basic than II (B) II is more basic than I and III
(C) ID is more basic than II (D) all are aromatic bases
Q.18 Which is/are untrue statements)?
(A) Protonation increases electrophilic nature of carbonyl group
(B) CF3S03 is better leaving group than CH3S0 3
(C) Benzyl carbonium ion is stabilised by resonance
/OH
(D)CC13CH<"
^ 0 1 1 is unstable.
Q.19 Which reacts with Ag N0 3 to give ppt. ?
(A)<0)-Br (B) <^0 )-CH=CH-CH 2 Br
(C)|Or- (D)(£>- B r
Q.20 Identify the correct statment(s).
0 1 II
(A) I & III are antiaromatic
III Oiv
(B) III & IV are non-aromatic
(C) II alone is aromatic (D) II & IV are non-aromatic
Q.21 Which have acidic hydrogen?
(A)CH3COOH (B)(0>-< OH
(C) C H 3 - C - C H 2 - C N (D) NaNH2
Q.22 C-C and C=C bond lengths are unequal in:

(A) benzene (B) 1,3 buta-di-ene
(C) 1,3 cyclohexa-di-ene (D)None
Q.23 Products formed when HC1 adds to 2,4- hexadiene is:
(A) 4-chloro-2-hexene (B) 2-chloro-3-hexene
(C) 2-chloro-4-hexene (D) 1 -chloro-2-hexene
Q.24 Which ofthe following may be classed as an electrophilic reagent?
(A)BCI3 (B) N H; (C) CH 3 (D)AlCi;

Q.25 The acid strength of substituted carboxylic acids is known to be dependent on the nature and position of
the substituent. In the following examples, an attempt has been made to arrange the acids in order of acid
strength, the strongest first. One of the series is incorrect-which one?
(A) CH3.CH 2CH(Cl).COOH > CH 3.CH(Cl).CH 2COOH > CH 3 .CH 2.CH 2.COOH
(B) NO2.CH 2.COOH > HOCH 2.COOH > CH 3.COOH
(C) Cl3C.COOH > BrCH 2.COOH > FCH2.COOH
(D) CH3.COOH > CH3.CH 2.COOH > (CH3)3C.COOH
Q.26 Which ofthe following would not have a dipole moment?
(A)CC14 (B)CH2C12 (C) trans-1,2-dichloroethene (D)C1C=CC1
Q.27 Which ofthe following structures represent the less stable tautomeric form?
(A)ch3ch2cK F^ 8^ o c h 2 .ch3 (B) N Qo

1
H
H
H
H(X YH
(D) /C = C
\
o
Q.28 Which ofthe following compounds cannot exhibit keto-enol tautomerism?
O
CH,
(A) (B)
X I u
H 3 C N H 3 C » CH3
(C ) H C/ C = 0 ( D ) H 3 C ^
3
Q.29 In tautomerism
(A) a proton is moved around the molecule (B) electrons are moved around the molecule
(C) no actual movement occurs (D) shift of double bond occurs
Q.30 Which species is not aromatic?

n
(A) ON (B)O (c)Cj (wt>
N9
Q.31 Aromatic character is possible only when
(A) six electrons are delocalized
(B) the molecule is cyclic and planar having delocalized (4n +2)n electrons where n = 1,2,3....
(C) alternate sigma (a) & pie (TC) bond are present.
(D) None is true
6 Bansal Classes GOC m
FXERC1SE-1II
Q. 1 Arrange the following compounds in decreasing order ofK eq for hydrate formation.
O
C C H
C 6 H 5 CO CH 3 C I ^ O ) - - 3
( ) (2)
o 0
N02-<O>-^CH3 CH3^0>-C-CH3
(3) «>
^Q.2 Arrange the following compounds in order of:
Decreasing SN1 reaction rate:
Ph
s f < 1 ^ P h
I Q CI Q
II[
§ aD ( ) av)
Q.3(a)Decreasing SN2 reaction rate:
a) (P) an)
(b) Explain which ofthese reactions would have the faster rate?
CH3
(i) CH3CH2CH2 + CH 3 N: > or (ii) CH3CH2CH2 + CH 3 NH 2 >

C1
CI CH3
•^JÂ Which compound is more stable explain

1! © ©
(a) CH3 - C - CH = N = N >
(b) CH 3 -CH = N = N >

Q. 5 Arrange the isomers of molecular formula C4H9C1 in order of decreasing rate of reaction with sodium
iodide in acetone.
Q. 6 Explain in which solvents these reactions are faster:
CH 3 sr
+ KOH in CH3OH or CH3CH2OH £ )

I
(b) CH3CH 2CH2CH2 + OH inCH3OH or 50% CH3OH, 50% H 2 0
CI
I ©
(c) CH3CH2CH2 + : cS N: in CH3CH20H or DMSO.
Q.7(i)Choose the member of the following pairs of unsaturated hydrocarbons that is more reactive towards
acid-catalysed hydration and predict the regiochemistry ofthe alcohols formedfromthi s compound.
(a) (b) ^ ^ ^ or
(I) (II)
© (n)
(c) I or
(I) (ID
(ii) Predict on the basis ofcabocation stability, which member of each of the following pairs hydrolyses at
the faster rate.
Jr Br
Br
(a) or I (b ) | or Br
(I) (H) a)
( o [ Q©
(ii)
Q. 8 Assuming that cation stability governs the barrier for protonation in H - X additions, predict which
compound in each of the pairs in parts (a) to (b) will be more rapidly hydrochlorinated in a polar solvent.
(I) (II)
(a) CH2 = CH2 or
® <o> (O
Q .9 Select the member of each pair that shows faster rate of SN2 reaction with KI in acetone.
CH3-CH2-CH2-CH2-C1 or CH3 - CH - CH2 - CI
I
CH3
(I) (II)
CH3 - CH2 - CH2 - CI or CH3 - CH2 - CH2 - CH2 - Br
(I) (II)
CH,
J0T CH3 - CH - CH2 - CH2 - CI or CH3 - C - CH2C1

CH3 CH3
(I) (II)
Br Br
I I
(d) CH3-CH2-CH2-CH-CH3 or CH3 - CH - C % CH - CH3
I
CH3
©
(P)
Halogen Derivatives
^Bansal Classes [15]
Q.16 Explain why CI - CH 2 - O - CH 2 - CH3 is hydrolysedmore rapidly than CH 3 - O - CH 2 - CH2 - CI

Q.17 Ifthe temperature is not kept below 25 °C during the reaction ofprimary alcohols with p-toluenesulfonyl
chloride in pyridine, it is sometimes observed that the isolated product is not the desired alkyl
p-toluenesulfonate but is instead the corresponding alkyl chloride. Suggest a mechanistic explanation for
this observation.
Q.18 Because the SN1 reaction goes though a flat carbocation, we might except an optically active starting
material to give a completely racemized. In most cases, however, SN1 reactions actually give more of the
inversion product. In general, as the stability ofthe carbocation increases, the excess inversion product
decreases. Extremely stable carbocations give completely racemic products. Explain these observation.
Q.19 cis-1 -Bromo-2-tert-butylcyclohexane and trans-1 -bromo-2-tert-butylcyclohexane both react with sodium
ethoxide in ethanol to give 1 -tert-butylcyclohexene. The cis isomer reacts much more rapidly than the
trans isomer. Explain.
Q.20 The reaction ofan amine with an alkyl halide gives an ammonium salt.
R:>N: + R'-x —> R3N - R ' X -
amine alkyl halide ammonium salt
The rate of this SN2 reaction is sensitive to the polarity ofthe solvent. Draw an energy diagram for this
reaction in a nonpolar solvent and another in a polar solvent. Consider the nature ofthe transition state,
and explain why this reaction should be sensitive to the polarity ofthe solvent. Predict whether it will be
faster or slower in a more polar solvent.
Q.21 There is an overall 29-fold difference in reactivity of 1 -chlorohexane, 2-chlorohexane towards potassium
iodide in acetone.
(a) Which one is the most reactive? Why?
(b) Two ofthe isomers differ by only a factor of2 in reactivity. Which two are these? Whcih one is the more
reactive? Why?
Q.22 The compound KSCN is a source of thiocyanate ion.
Write the two most stable Lewis structures for thiocyanate ion and identify the atom in each that bears a
formal charge of-1.
Q.23 With the help of following data show HBr exhibits the peroxide effect.
A H, 0 AH 2 °
H-X x + CH 2 = CH 2 X CH , - C H 2 X C H 2 - C H 2 + H - X - > X CH 2 CH 3 + x
I
HQ -67 +12.6
HBr -25 .1 - 50.2
HI +46 -117.1
All are in kJ mole '.
Q.24 CHC1,F is found to react more slowly than CHC1, in alkaline hydrolysis with plausible mechanism.
Illustrate this phenomenon. vaoA*-**-

Q.25 Formulate the reactions between but-l-ene in presence of small amount ofbenzoyl peroxide &
(i)CCl4 (ii)CBrCl3
Give your reasons.
Q.26 p-Amino benzaldehyde behaves like an amide as is evident by the fact that it is not readily attacked by
the nucleophile at the carbonyl carbon. Explain.
Q.27 When CH3MgBr react with 5-chloro-2-pentanone, cyclic ether is formed instead of alocohol. Explain.
Q.28 The dichlorocarbene reacts with electron rich species like phenol where as it doesn't reacts with benzene
explain.
tBansal Classes GOC ]l7J
Q.29 Explain the following:

(a) 3-pentanol reacts with HBr to give a mixture of 3 & 2- bromopentane. The exact composition of the
mixture depends upon whether gaseous or aqueous HBr is used.
(b) Hydration of 3-phenyl-1-butene in dil H2 S0 4 is not a satisfactory method for preparing
3-phenyl-2- butanol
Q.30 Why is elimination preferred to hemiacetal formation in the acid catalysed cyclisation of this ketone ?
O o
-OCX
D1
0 ' ^ o
Q.31 CH2 = CH - CH2 CH2 - C ~ OH ( Cyclic ester)
a 3
* (lactone)
This type ofreaction is called "bromolactonistaion". Suggest a mechanism.
Q.32 Draw mechanisms for these reactions, explaining why these particular products are formed.
Q
MeOH F T
Q.33 Write a reasonable and detailed mechanism for the following transformation.
C X ^ y < cone. > r Y<f+H20

OH H2SO4
Q.34 The reaction of cyclopentyl bromide with sodium cyanide to give cyclopentyl cyanide
f y H NaCN ) , r \ H
k / \ r ethanol-water
Cyclopentyl bromide Cyclopentyl cyanide
proceeds faster if a small amount of sodium iodide is added to the reaction mixture. Can you suggest a
reasonable mechanism to explain the catalytic function of sodium iodide?
Q.35 The reaction of 2,2-dimethyl-1 -propanol with HBr is veiy slow and gives 2-bromo-2-methyl-propane
as the major product.
CH, CH,
I r
I
CH3CCH2OH f* c > CH3CCH2CH3
CH3 Br
Give a mechanistic explanation for these observations.

Q.36 1-Bromobicyclo [2.2.11 heptane (the structure ofwhich is shown) is exceedingly unreactive towards nucleophilic
substitution by either the SN, 1 or SN,2 mechanism.
Br
1 -Bromobicyclo [2.2.1 ] heptane
Halogen Derivatives
Q. 3 7 We saw that acid-catalyzed dehydration of2,2-dimethyl-cyclohexanol afforded 1,2-dimethylcyclohexene

To explain this product we must write a mechanism for the reaction in which a methyl shift transform
secondary carbocation to atertiary one. Another product of the dehydration of 2,2-dimethyIcyclohexanol
is isopropylidencyclopentane. Write a mechanism to rationalize its formation.
Cte ^ CC3 + O^to

CH3
2,2-Dimethylcyclohexanol 1,2-Dimethylcyclohexene Isopropylidenecyclopentane
Q.3 8 When 2-bromo-2,3-dimethylbutane reacts with a base under E2 conditions, two alkenes (2,3-dimethyl
1-butene and2,3-dimethyl-2-butene) are formed.
(a) Which ofthe following bases would give the highest percentage of the 1 -alkene ?
(b) Which would give the highest percentage ofthe 2-alkene"
CH3 CH2CH3 CH3
CH3CO~ CH3CH2CO~ CH3CH20_ CH3CH2CO~
CH3 CH2CH3 CH3

^Q.39 Dr. Don T. Doit wanted to synthesize the anesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion
and 2-chloro-2-methylpropane for his synthesis and ended up with very little ether. What was the
predominant product of his synthesis ? What reagent should he have used ?
Q .40 The following reaction takes place under second-order conditions (strong nucleophile), yet the structur
ofthe product shows rearrangement. Also, the rate ofthis reaction is several thousand times faster than
the rate ofsubstitution ofhydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism
to explain the enhanced rate and rearragement observed in this unusual reaction. ("Et" is the abbreviatio
for ethyl.)
Et2N: :NEt2
I I
H2C-CH-CH2CH3 "OH ) H2C-CH -CH 2 CH 3 +cr
CI OH
*Q.41 When ethyl bromide is added to potassium t-butoxide, the product is ethyl t-butyl ether.
+
CH3CH2 - Br + (CH3)3C - 0~ K > (CH3)3C - O - CH2CH3
ethyl bromide potassium t-butoxide ethyl t-butyl ether
(a) What happens to the reaction rate ifthe concentration of ethyl bromide is doubled ?
(b) What happens to the rate ifthe concentration ofpotassium t-butoxide id tripled and the concentration o
(c) ethyl
Whatbromide
happensistodoubled
the rate?ifthe temperature
* is raised ?
Q. 42 Give a mechanism to explain the two products formed in the following reaction.
Hx /CH 3 Br CH3
H\ X H\ X I ^ C " C H3
C = c XCH 3 NBS,hv C- C
X
CH 3 + Br—C-C
H/ % H/ \h I
H
X
H
3-methyl-l-butene not rearranged rearranged
Halogen Derivatives
Q.4 3 Give the structures of all possible products when 2-chloro-2-methylbutane reacts by the El mechanism.
Q .44 Solvolysis of 1,2-dimethylpropyl p-toluenesulfonate in acetic acid (75°C) yieldsfivedifferent products:
three are alkenes and two are substitution products. Suggest reasonable structures for thesefiveproducts.
Q.45 Solution A was prepared by dissolving potassium acetate in methanol Solution B was prepared by
adding potassium methoxide to acetic acid. Reaction of methyl iodide either with solution A or with
solution B gave the same major product. Why ? What was this product?
Q .46 Identify
Solvolysis of 2-bromo-2-methylbutane in acetic acid containing potassium acetate gave three products.
them.
Q.47
(a) Write the structures or build molecular models of all the isomeric alkyl bromides having the molecular
formula C5HnBr.
(b) Which one undergoes E1 elimination at the fastest rate ?
(c) Which one is incapable of reacting by the E2 mechanism ?
(d) Which one can yield only a single alkene on E2 elimination ?
(e) For which isomers does E2 elimination give two alkenes that are not constitutional isomers ?
(f) Which one yields the mobt complex mixture of alkenes on E2 elimination ?
Q.48 Evidence has been reported in the chemical literature that the reaction
(CH3CH2)2CHCH2Br + KNH2 > (CH,CH2)2C - CH2 + NH3 + KBr
proceeds by the E2 mechanism. Use curved arrow notation to represent the flow of electrons for this
process.
Q.49 The given compound give mixture of six products on treatment with CH3OH. Write structures of all five
products and give mechanism of the reaction.
Q.50 Comment on the selectivity, (that is, say what else might have happened & why it didn't) shown in this
grignard addition reaction used in the manufacture of an antihistamine drug, A.
CI
Q. 51 Outline an efficient synthesis ofeach of the following compoundsfromthe indicated starting material and
any necessary organic or inorganic reagents:
(a) Cyclopentyl cyanidefromcyclopentane.
(b) Cyclopentyl cyanidefromcyclopentene.
(c) Cyclopentyl cyanidefromcyclopentanol.
(d) Isobutyl iodidefromisobutyl chloride.
(e) Isobutyl iodidefromtert-butyl chloride.
(f) Isobutyl azidefromisopropyl alcohol
Q. 5 2 Select the combination of alkyl bromide and potassium alkoxide that would be the most effective in the
synthesis ofthe following ethers:
Halogen Derivatives
^Ban sal Classes [20]
Q. 5 3 Indicate the major alkene produced by each of the following

Br
ch
(a) CH 3 -CH 2 -CH 2 -C -CH3 3'§k/a >
CH3
CH3
(b) CH 3 - C H 2 - C H 2 - C - N ( C H 3 ) 3 OH^->
CH3
CH3
(c) (CH3)3 N- C - CH2 - CH3 O H >

CH3 f
(d) CH 3 -CH 2 -CH 2 -CH-CH 3 (CH
3>3COK >
Q.54 Choose the compound of molecular formula C7H13Br that gives each alkene shown as the exclusive
product of E2 elimination.
(a) ( 3 ( b ) ( ^ CH 2 ( c )<> C H 3
CH, r A /CH(CH3)2
(d) (6) L ^ C H = CH2 ( f )|Q
k/cH3
(g)J^C(CH3)3
Qx5 5 Select the alkyl halide and a nucleophile that will give each of the following products.
^ CH3 - CH2 - CH2 - NH2 t/(fT) CH3 - CH2 - O - CH2- CH3
(c)CH = C- CH 2 -CH 2 - CH 3 Jdf(CH3)2CHS(CH3)2
Je)C6H5-0-CH2-CH3
Q. 5 6 Identify the product in each of the following reactions:
(a) C1CH2CH2CHCH2CH3 - i ^ ! l - > C 5 H 1 0 C l I

CI
(b) BrCH,CH2Br + NaSCH2CH2SNa > C4HgS2
(c) C1CH2CH2CH2CH2C1 + Na2S » C4H8S
Q. 5 7 Write the structure ofthe principal organic product to be expected from the reaction of 1 -bromopropan
with each ofthe following:
(a) Sodium iodide in acetone.
O
v (b) Sodium acetate ( CH3CONa ) in acetic acid.
(c) Sodium ethoxide in ethanol.
\Jd) Sodium cyanide in dimethyl sulfoxide.
Sodium azide in aqueous ethanol
^(fjSodium hydrogen sulfide in ethanol
w (g) Sodium methanethiolate (NaSCH3) in ethanol.
^Bansal Classes GOC 12U
Q.5 8 Predict the products of the following SN2 reaction:

NaLN
C 6 H 5 -C H 2 - C H 2 - B r > Jbf CI
C H 3 - ( C H 2 ) 8 - C H 2 - C I - ^ > (d) 0 ^ C H 3 I - >
Na0H
(e) HO - CH2 - CH2 - CH2 - CH2 - CI >
Q. 5 9 Draw each ofthe following reaction in a way that clearly show the stereoisomerism of the products.
H CH3
me
(a) CH3 - C - Br + CH3ONa ^01 > (b) CH3 - CH2 - C - Br + CH3OH —
C H 2 - C H 3 C 3 H 7
Na SH
(c) SN1
Q.60 What will be the products (A, B, C) in the folowing reaction?
RCH = CH2 ^ A
CC14 hv BrCCA
hv
C
Give a mechanism for each of the reactions.
Q. 61 Complete the following reactions. Give all possible products in each case. Give mechanism ofthe reactions.
C H 3 HOWA
(a) V Moist Ag 2 Q ) (b) CH 2 -CI >
^CH2C1
Q.62 Identify (A) to (D) in the given reaction sequence.

CH - CH, - CH, B * / h v ) (A) a l c Af H > (B) (C) - LlF
> (D)
Peroxide DMF
Q.63 Identify (A) to (E) in the given reaction sequence

Li/CuX
CH3-CH2-Br > (A) CH3-CH2-Br^ (B) ci2/hv ) ( C )+( D )+( E ) ( c ^ c S f > ( F ) + ( G ) + ( H )
Q. 64 Complete the following reactions:

O O
(a) CH3 - C - ( C H 2 ) 4 - C - CH3 (0I2/NaOH/A > ( A ) + ( B )
(ii) H®
o
c c h (i)Br2/ a H
(b) r v - 3 a ° >(Q+(D)
\ / (ii) H
(c)| >-CHOH-CH 3 (i) CaOCl^/HO H > ( E ) + ( F )
(ii) H
Na0H/F
(d) CH3 - CH - CH2 - CH3 ^ >G +H
CI
Q.65 Complete the following reactions

Electrolysis
(a) C 6 H 5 - CH - CH 3 + NaCl + HOH > A sweet smelling liquid
Br
XI
aq.NaOH
(b) C 6 H 5 - CH
-CI
Q.66(i)What are the products of the following reactions ?
\ / 3
(a) PhCH = CHCH 3 + HBr >A (b) /c = c
\N +HI >B
H3 C H
CH,
Peroxide
(c) l ^ J + HBr >C (d) + HC1 >D
CH 2 CH 3
(ii) What are the products ofthe following reactions ?

2
(a) PhC 5= CH + Br 2 » (b)
w CH33 CH,CH
2 = CH,
2
H?0 >
CH3 Br Na0H
Br, VC =- nCH
u2 2 v> v>
(A\
(c) H-tO K ) H
H3C "2° 2°
Q.67 What products would be formed in these reactions ?
(i)EtMgBr
CI
v
(i)PhLi
(a) Ph - C = CH (ii)ph2C0 A (b) -»B
(iii) NH4C1 (ii)C02 ,(iii)H /H 2 0
O
II
Q.68 CH3CH2CH 2C1 ale.KOI 1 ^ A S02C12 ) q Mg/Et2Q c (i)CH3-C-CH3 ) p H2SQ4/A ) ^
(ii)aq.NH4Cl
o
Q.69 CLC - <!! - OH + Na >A - — > B. Find out A & B.
CHt-CHO
Q. 70 Give product and suggest mechanism for these reactions.
MeOCHjCl CHBft
?
->9 ® N^CO.E. 7
' < BuLi BuOK
Ph - CH = CH
ABansal Classes GOC [23]
EXERCISE-IV (A)
^pd Reaction of R-CO-NH 2 with a mixture of Br2 and KOH gives R-NH2 as the main product. The
intemediates involved in this reaction are: [JEE 1992]
(A) R-CO-NHBr (B)RNHBr
(C) R-N=C=0 (D) R.CO.NBr2
Which one ofthe following has the smallest heat of hydrogenation per mole? [JEE 1993]
(A) 1-Butene (B) trans-2-Butene
(C) cis-2-Butene (D) 1,3-Butadiene
In the following compounds: [JEE 1996]
OH OH
NO,
(I) (HI)
The order of acidity is:

(A) III > IV > I > II (B) I > IV > III > II (C) II > I > III > IV (D) IV > III > I > II
v^4 OHwi
OH with HBr gives: [JEE 1998]
(A) CHXHBrCH
•O (B)CH H CHBr
3 2
O OH
(D) CH CH CHBr -TV.
Q.5
(C) CHXHBrCH.
o 3 2 ^~Br
A solution of (+) 1 -chloro-1 -phenylethane in toluene racemizes slowly in the presence of small amount
of SbCl5 due to formation of: [JEE 1999]

(A) carbanion (B) carbene (C) free radical (D) carbocation
An aromatic molecule will: [JEE 1999]

(A) have 4n n electrons (B) have (4n+2) n electrons
(C) be planar (D) be cyclic
Q.7 The enol form of acetone, after Prolonged treatment with D 2 0, gives: [JEE 1999]
OD O OH OD
I I
(A) CH 3 - C = CH2 (B) C H 3 - C - C H 3 (C) CH2 = c - C H 2 D (D) CD2 = C-CD 3
Amongst the following, the most basic compound is: [JEE 2000]
(A) C6H5NH2 (B) p-N0 2-C 6H4NH2 (C) m-N02-C 6H4NH 2(D) C6H5CH2NH2
Q.9 An SN2 reaction at an assymetrical carbon of a compound always gives: [JEE 2001]
(A) enantiomer of the substrate (B) a product with opposite optical rotation
(C) a mixture of diastereomeres (D) a single stero isomers
Halogen Derivatives
[JEE 2001]
Q^M) The correct order of basicities of the following compounds is:
CH,—C (CH3)2NH CH 3CNH

NH2
(1) (2) (3) (4)
(A) 2 > 1 > 3 > 4 (B) 1 > 3 > 2 > 4 (C) 3 > 1 > 2 > 4 (D)L
Q.ll Identify the correct order of reactivity in electrophilic substitution reaction of the following compounds:
(1) (2) (3) (4)

(A)1>2>3>4 (B)4>3>2>1 (C)2>1>3>4 (D) 2>3>1>4 [JEE 2002]
^12 Left to right sp2, sp2, sp, sp hybridization is present in: [JEE 2 0 0 3 1
(A) H2C = CH-C=N (B) H2C=C=CH-CH3 (C) H O C - O C H (D) HOC-CH=CH 2
Maximum dipole moment will be of: [JEE 2003]

(A) CCL (B)CHC1 3 (C)CH2C12 (D)CH3C1
COOH
Q.14
[JEE 2003]
when X is made to react with 2 eq. of NaNH2 the product formed will be:
(A)
(C)
GOC [25]
fa Bansa! Classes
Q.15 Order of rate ofreaction of following compound with phenyl magnesium bromide is: [JEE 2004]
Ph-C-Ph Me- C-H Me-C- Me
I! II II
O o o
(I) (II) (III)
(A) I > II > III (B) II > III > I (C)III>I>II (D) II > I > III
Hs
YVV5™ 3 [JEE 2004]
Q.16
COOH
X
Correct order of acidic strength is:

(A) x > y > z (B) z > y > x (C) y > z > x (D) x > z > y
Q.17 1 -Bromo-3-chloro cyclobutene on reaction with 2-equivalent of sodium in ether gives [JEE 2005]
.CI
(A) j <B (C) (D)
•
Cf
JSO 3H
O , H C
f o l CH 3 COONa(excess)
[JEE 2005]
Q.18 \ J (absolution)
SO2COOCH3
(A) (B)
Me
S0 3 Na COONa
(C)(0) +CH3COOH (D)lOJ + H 2 S0 3

Me Me
Q.19 Conversion of cyclohexanol into cyclohexene is most effective in [JEE 2005]

(A) concentrated H 3P0 4 (B) concentrated HCl
(C) concentrated HCl / ZnCl2 (D) concentrated HBr
CH,
I [JEE 2005]
Q.20 Ph - MgBr + CH3 - C - OH »A
I
CH,
CH, OH CH,
3
I I
(A) (D) CH3 - C - Ph
( B ) C H 3 -C-OPh (C)
CH, CH,
Q.21 For 1 -methoxy-1,3-butadiene, which of the following resonating structure is the least stable?
(A) H 7 C- CH- CH = CH - O - CH, (B) H 2 C- CH = CH - CH = O - CH3
(C) H2C = C H - C H - C H - 0 - C H 3 (D) H2C = CH - CH- CH = O - CH3

[JEE 2005]
CH3 H CH3
Q.22 MCO-^5^- ^5}"N02 [JEE 2005]
H CI CH3
on hydrolysis in presence of acetone

CH3 H CH3 CH3 H CH3
(K) M e O ^ O ^ - -<p)-N02 ( L) Me O - <g > - ^ Q } -NO,
H OH CH3 OH H CH3
CH3 H CH3
(M) Me O - Ô ) - -(O)-^02
H CH 3 OH
(A) K & L (B)only (C)Monly (D) K & M
Q.23 When benzene sulfonic acid and p-nitrophenol are treated with NaHC0 3, the gases released respectively
are [JEE 2006]
(A) S02 , N0 2 (B) S0 2 , NO (C) S0 2 , C0 2 (D) CO2, CO2
CH3NH2 + CHC13 + KOH -» Nitrogen containing compound + KC1 + H2 0. Nitrogen containing

compound is [JEE 2006]
(A) CH3-C s N (B) CH3-NH-CH3 (C) CH3 - N = C (D) CH3 N = C
^25 (I) 1,2-dihydroxy benzene (II) 1,3-dihydroxy benzene [JEE 2006]
(HI)increasing
The 1,4-dihydroxy benzene
order (IV) Hydroxy
of boiling points ofabove mentioned benzene
alcohols is
(A) I <II< III< IV (B) I <II<IV<II I (C) IV<I <II <II I (D) IV<I I<I< III
fa Bansa! Classes GOC [27]
Question No. 26 to 28 (3 questions)

Comprehension I
RCONH2 is converted into RNH2 by means ofHofmann bromamide degradation,
(i) OM (ii) V (iii)

=
H2N^Q-CI ^ <N HQ - CI
(vi) (v) (iv)
In this reaction, RCONHBr is formedfromwhich this reaction has derived its name. Electron donating
group at phenyl activates the reaction. Hofinann degradation reaction is an intramolecular reaction.
How can the conversion of(i) to (ii) be brought about? [JEE 2006]
(A)KBr (B)KBr + CH3ONa (C) KBr + KOH (D) Br2 + KOH

^27 Which is the rate determining step in Hofmann bromamide degradation? [JEE 2006]
(A) Formation of (i) (B) Formation of (ii) (C) Formation of (iii) (D) Formation of (iv)
Q.28 What are the constituent amines formed when the mixture of (i) and (ii) undergoes Hofinann bromamide
degradation?
D
(i) (ii)
I \-NH 2 $ \- NH 2 R V - •NH,
N
(A) > = / )=/ ' \ =/
D D
Q-NH 2 ) Q-MH2 (C) i \- NH 2 $ \-NH;

(B) > = / ' W (C)
D
(D) ^ y - N H D ) ^ y [JEE 2006]
Halogen Derivatives
EXERCISE-IV (B)
Q. 1 CH 3CH 2CHC1 2 "1-KOH > ? [JEE 1991]
a1c1 [JEE 1992]

Q.2 C 6 H 6 + (CH3 )2 CHCH2 C1 3 >?
Q.3 ( O V C O O ^ O ) , [JEE 1993]

\ _ y X / monomtration
Q. 4 Draw the stereochemical structure of the products in the following reaction: [JEE 1994]
CNH<
_H NaOH > ?
BR-
SM2
CH,
Q. 5 Complete the following, giving the structures ofthe principal organic products: [JEE 1997]
(a) + KNH 9 •
(b) \\ / I + CHBr 3 +1 - BuOK >B
(c) ClCH2 CH 2 CH 2 COPh + KOH + MeOH >C
Q. 6 Write the intermediate steps for each ofthe following reaction. [JEE 1998]
H,0
® C 6 H5 CH(OH) C=CH > C 6 H 5 CH = CH-CHO
• o c r ^ o a ,
Q.7 Each of the following reaction gives two products. Write the structure of the products. [JEE 1998]
AlcK0H A
(a) C 6H5 CH 2 CHC1C 6H5 ' >
Br
(b) CH 3 CONHC 6 H 5 2.Fe )
Q.8 Out of anhydrous A1C13 and hydrous A1C13 which is more soluble in diethyl ether? Explain with reason.
[JEE 2003]
Q.9 Match K a values with suitable acid: [JEE 2003]

K Acid
® 3.3 x 10"5 (a) <0)-

C O O H
(ii) 4.2 x 10"5 (b) Me-^^-COOH
Cm) 6.3 xlO" 5 (C) C ^ C O O H
(iv) 6.4 x 10"5 (d) MeO^COOH
(v) 30.6 x 10~5 (e) COOH
fa Bansa! Classes GOC [29]
Q.10 Give resonating structures of following compound. [JEE 2003]

Y V
OH
Q. ll Which ofthe following is more acidic and why? [JEE 2004]
IJH3
.6; .o.
Q.12 Predict whether the following molecules are iso structural or not. Justify your answer. [JEE 2005]
(i)NMe3 (ii)N(SiMe3)3
H,C
Br
(a) (0 c2H5OH(aq.) ^ acidic solution
CH,
3
(ii) B r _ / " \ _ y C2H5OH(aq.) ) ne ut ral
\ = / rCH,
Na H(aq)
(b) (i)0, N ^V ° >F (liberated)
CH,
NaOH(aq.) . p i s n o t liberated
(ii)
H,C
H2N02
Conc.HNOg
(c) (i)
Conc.H2S04
NO,
NO, NO,
Conc.HNO
(ii) I
Conc.H2S04
NO,
(d) is formed but not
Q.10 Give resonating structures of following compound. [JEE 2003]

Y V
OH
Q. ll Which ofthe following is more acidic and why? [JEE 2004]
NH, NH 3
OJ IC>
Q.12 Predict whether the following molecules are iso structural or not. Justify your answer. [JEE 2005]
(i)NMe3 (ii)N(SiMe3)3
H3C
Br
(a) © c2H5OH(aq.) ^ acidic solution
CH3
CH
(ii)Br-7^W C2H5OH(aq.) > neutral
\=j rCH,
Na H(aq)
(b) (Oo.N^V ° > F (liberated)
CH,
NaOH(aq.) ) p is not liberated

(ii)
H,C
CH 2 N0 2
.0
O
Conc.HNO,
(c) (i) > N02 + |
Conc.H-.SO
2JU4
NO,
NO, NO,
Conc.HNQ3
(ii) I
Conc.H2S04
NO,
(d) is formed but not
NaBr+Mn 2
Q.14 ° A— ConcHN0 3 ) C( in te rm ed ia te )- ^^ D(Explosiveproduct)
FindA ,B ,C and D. Also write equations Ato Band Ato C. [JEE 2005]
Q!5 H a . - I w [JEE 2005]

where is the dipole moment of stable conformer and x{ is the fraction of that conformer.
(a) Write stable conformer for Z - CH 2 - CH 2 - Z in Newman's projection. If psolutjon = 1.0 D and mole
fraction of anti form = 0.82, find
(b) Write most stable meso conformer of CHD Y
I
CHDY
If (i) Y=C H 3 about C2 - C 3 rotation and (ii) Y= OH about Cl - C2 rotation.
Halogen Derivatives
faBansal Classes [31]
ANSWER KEY
EXERCISE-I
Q.l D Q.2 C Q.3 B Q.4 B Q.5 B Q.6 A Q.7 A
Q.8 D Q.9 A Q.10 B Q.ll A ' Q.12 C Q.13 C Q.14 C
Q.15 C Q.16 A Q.17 B Q.18 B Q.19 C Q.20 A Q.21 D
Q.22 A Q.23 C Q.24 C Q.25 D Q.26 A Q.27 D Q.28 C
Q.29 A Q.30 C Q.31 B Q.32 B Q.33 C Q.34 B Q.35 B
Q.36 A Q.37 A Q.38 C Q.39 B Q.40 D Q.41 B Q.42 A
Q.43 A Q.44 A Q.45 A Q.46 C Q.47 C Q.48 C Q.49 A
Q.50 D Q.51 D Q.52 C Q.53 C
EXERCISE-II
Q.l C Q.2 A,D Q.3 A,B,C,D Q.4 A,B,C,D
Q.5 B,C,D Q.6 A,B,D Q.7 A,B,D Q.8 C
Q.9 C,D Q.10 A,B Q.ll A,B Q.12 A,D
Q.13 A,C,D Q.14 C,D Q.15 D Q.16 A
Q.17 B,D Q.18 D Q.19 B,D Q.20 A,C
Q.21 A,B,C Q.22 B,C Q.23 A,B Q.24 A,C
Q.25 A,D
Q.29 C Q.26 A,C,D
Q.30 B Q.27 A,B,C
Q.31 D Q.28 D
EXERCISE-III
Q.l 3>2> 1 >4 Q.2 IV > I> II > II I Q.3 (a )I I> I> II I> IV ; (b) (ii)
C
Q.4 (a) Q.5 C-C-C-C-C 1 > C - C - C - C l > C - C - C - C l > C - C - C l
c c c
Q.6 (a) II, (b) I, (c) II Q.7 (i) (a) II, (b) I, (c) II ; (ii) (a) II, (b) II, (c) I
Q.8 (a) II, (b) I Q.9 (a) I, (b) II, (c) I, (d) I Q.10 (a) II, (b) I, (c) II, (d) II
Q .11 (a) H; 03)11; (c) I ; (d) H; (e) n Q.14 b,d,e,g,h Q .15 a,c ,e, f,g ,h
y O s x
Q 2.1 I | Q.38 (a) Et3CO®; (b) EtO® Q.45 MeCOOMe
OAC
Q.46 C - C - C - C , C-C = C-C , C - C - C - C
C C c
c c
Q.47 (b) C - C - C - B r ; (c) B r - C - C - C ; (d) C-C-C-C-C-Br; (e) C - C - C - C - C
C C Br
(f) C-C-C-C-C
Halogen Derivatives
faBansal Classes
[32]
Q.50
C C
Q. 53 ( a ) C - C - C = C - C ; ( b ) c - C - C - C = C 5 (<0 C = C - C - C ; (d) C - C - C - C= C
C
Br CH,Br
Q.5 4 (a) ; (b ) ; (c) B r - - ( ^ ) - C H 3 ; (d) L y ^ ; (e) Q>-CH 2 - C H 2 -Br
(f)
B r ^ ' ^ [ ^ - C Me s
Q.55 (a) CH 3 CH 2 CH 2 C1 + N H 3 ; (b) CH 3 CH 2 ONa + CH 3 CH 2 C1; (c) HC°C®Na e + CH 3 CH 2 CH 2 -C1

(d) Me 2 CH-Cl + Me 2 S ; (e) C 6 H 5 ONa + CH 3 CH 2 -C1
Q.56 (a) IC H 2 CH 2 - C H - C H 2 C H 3 ; (b) ; (c)
CI
Q.57 (a) ; (b) ; (<» ; (d) / ^ C N ; (e) ; (f) ^ / S H ; (g)

o
Q.58 (a) C 6 H 5 -CH 2 -CH 3 -CN, (b) <^>-SCH 3 , (c) CH 3 -<CH 2 ) 9 -I, (d) <ON®- ch 3 I 0 , (e)
H Me Me
Q.59 a)CH 3 0 - C - C H 3 ; (b) Et -C -O Me + Me O- C- Et , (c) +

Pr Pr
CH 2 CH 3
SH
Q.60 (A)RCH 2 CH 2 SR (B)RCHBrCH 2 CCl 3 (C) RCHC1CH 2CC13
Q.62 CH 3 -CH 2 -CH 2 -F
Q.64 (a) CHI 3+(CH2 )4 (COOH) 2 , (b) CH Br 3 + Q - C O O H , (c) CHCl 3 +[>-COOH, (d) CHF 3 + EtCOONa
Q.65 (a)CHCl 3 , (b)PhCHO
/
Q.66 (i) (a) P h - C H - E t , (b) Me2C (I )-Et, (c) (d) \ ^
Et
Br
(ii)(a)^>C=C<«r, (b) Et-CH-CH2-Cl, ( df )
OH
Ph ph
I ^k/COOH
Q.67 (a) Ph - C = C - C - Ph; (b) f O j
Ph
Q.68 Me 2 C=CH-CH=CH2
Q.69 A::CC1 2 B:
CI CI
0 M e
Q.70 (i) & Ql>- ; (ii) r h A , COOEt
EXERCISE-IV (A)
Q.2 D Q.3 D Q.4 B Q.5 D

Q.l A, C
Q.6 B, C, D Q.7 D Q.8 D Q.9 D Q.10 B
Q.ll C Q.12 A Q.13 D Q.14 C Q.15 B
Q.16 D Q.17 C Q.18 C Q.19 A Q.20 A
Q.21 C Q.22 A Q.23 D Q.24 D Q.25 C
Q.26 D Q.27 D Q.28 B
EXERCISE-IV (B)
C(CH3) 3
Q.l CH 3CH 2 CHO Q.2 [ Q Q.3 ^ C O O -Q^

CH,
Br o
Q.4 C 6 H 5 - C - C H3 Q.5 (A) PhC=CPh, (B) , v(C)J II / \
Ph-C-CH—CH,
CH,
Halogen Derivatives
h
Q.6 C6H5-CH-CeeCH > C 6 H 5 - C H - C = C H — 5 ^ - > C 6 H 5 - C H - C = CH
OH ®OH
H2
C 6 H 5 - CH = C = CH ° > C 6H5 - C H = C = C H
+
OH 2
C 6 H 5 - CH = C = CH tautomerism , C6 H5 ~CH=CH-CHO
I "
OH 2
-FT
o^ch 3 " - c r X :H 3
H
NHCOCH 3 NHCOCH 3
H H
Q.7 (a) (b) [ f +r j
( Ma jo r) l^JJ
Br
Q. 8 Anhydrous A1C13 is more stable then hydrous A1C13 because it is having vacant 3p orbital of A1 which can
accept lone pair of electrons from oxygen of diethylether.
Q.9 (iHd), (hH b) , (iiiHa), (ivHc), (v He ) Q.10 ^
compound.
Q.12 Not. NMe 3 is trigonal pyramidal while N(SiMe 3) 3 is trigonal planar due to back bonding.
Halogen Derivatives
CH.3
Q.13 (a) (i) H5C6 - C - OC2H5 + HBr(acid); (ii) no reaction due to partial double bond character
CH,l3
(b) (i) 02N + F~ is liberated; (ii) Bimomecular mechanism is not possible in (ii) case
CH3
(c) (i) due to presence of lone pair of nitrogen atom NO group is electron denating and ortho, para
directing
(ii) N0 2 group is electron withdrawing and meta directing
(d) Due to reduction of centralring,three four membered antiaromatic rings become stable while on
recuction ofterminal ring only one antiaromatic ring can be stabilized.
CH3
O2N> -NO2
Q.14 (A)H 2S0 4, (B)Br2, (C) NO®, (D)
NO 2
D
\
-OH
Q-15 (a)^Gauch = 5.55D;(b)(i)
H •H
CH3 H
faBansal Classes GOC [36]
[[organic chemistry!
XII (AL L )
HALOGENDERIVATIVES
CONTENTS
EXERCISE-I (A)
EXERCISE 1(B)
EXERCISE-II
EXRECISE-III
EXRECISE-IV(A)
EXERCISE IV(B)
ANSWER KEY
EXERCISE-I (A)
(Choose the correct option. Only one is correct)
Q lf Which one is liquid at room temperature:
^ (A)CH3C1 (B)C2H5C1 (C)CH3Br (D)C2H5Br
^L The correct order ofmelting and boiling points of the primary (1 °), secondary (2°) and tertiary (3°) alkyl
halidesis:
(A)P >S>T (B)T> S>P (C) S> T> P (D) T>P >S
Q?f Pick up the correct statement about alkyl halides:
(A) They show H-bonding (B) They are soluble in water
(C) They are soluble in organic solvent (D) They do not contain any polar bond
Q.4 What would be the product when neopentyl chloride reacts with sodium ethoxide:
(A) 2-Methyl-2-butanol (B) Neo pentyl alcohol
st nd
(C) Both 1 & 2 (D) 2-Methyl-2-butene
5 Reduction of alkyl halide by LiAlH4 is the type of reaction:
(A) Nueleophilic substitution reaction (B) Electrophilic substitution reaction
(C)Electrophilic Addition reaction (D) None of these
Q. 6 2-methyl
(A) butanoic acid(B)Ethene
Propene is formed by the reaction CHC13, NaOH and (D)2-Butene
(C)l-Butene
Q.7 CC14 + KOH (excess) » end product of the reaction is:
(A) K2C03 (B)C0 2 (C) C (OH)4 (D)HCOOK
Q. 8 The yield of alkyl bromide obtained as a result of heating the dry silver salt of carboxyic acid with
bromine ifCC14 is:
(A) 1°> 3° >2° bromides (B) 1°> 2° >3° bromides
(C) 3° > 2° > 1° bromides (D) 3° > 1°> 2° bromides
Which of the following statements is invalid:
(A) The more stable the carbocation the faster it is formed
(B) Propyl cation changes to more stable isopropyl carbocation by 1,2 shift of a hydrogen
(C) Isopropyl chloride reacts with sodium ethoxide to form 1-ethoxypropane
(D) Propyl halides reacts with sodium ethoxide to form 1-ethoxypropane
Q.10 Nitrochloroform is prepared by the action of chloroform and:
(A) Hot aqueous solution ofKN03 (B) Hot aqueous solution ofNaN02
(C) Hot concentrated nitric acid (D) Hot dilute HC1 + aq. NaN02 solution
, Odl Which of the following compounds is most rapidly hydrolysed by S^l mechanism.
(A)C6H5CI (B) C\-CU2-CU=CU2
(C)(C6H5)3CC1 (D)C6n5CU2C\
o
H
Q.12 CH3MgBr + CH2 = CH - C - H 2° > product (major), product is
OH
(A) CH2 =C H -C -H (B) CH 2 -CH = CH-CH 3

i i
CH3 OH
(C) CH3-CH2-CH2-CHO (D) None is correct
n BuLi
Q.31 n-CjgH^Br + HC =CNa >A - > B
H /Imc ar scat p6roxybenzoicacid
5-methyl-1 -hexene + HBr (peroxides) -> C - ^ D ^ " ' - >E >F
Q.32 Complete the following by providing (A), (B),(C) and (D):

PBr Alc K0H HBf NH
(i) CHjCH^CHjOH 3 > (A) - > (B) > (C) ? > (D)
(ii) CH3CH2CH2I A16^011 > (A) h+/h

2 ° > (B) socl
2 > (C) (D)
LiAlH4
Alc K0 H HBr
(iii) CH3CH2CH = CH2 - J i ^ U (A) > (B) > (C)
Light
CH CHQ/H AlcKOn
(iv) CHgCH^MgBr 3 2° > (A) - ^ - > ( B ) > (C)
Q. 3 3 Carry out following conversions.

CI
I
(a) CH3 - CH - CH3 > C^ -C Hj -C Hj -C l without using peroxide
(b) CHg-CHj -CHj-Cl > CH3 -CH-CH3 in single step
CI
CH Br
(c)(^J > j^j in three steps only
C1
/"\^ C H 2 C 1
(d) ^ J j > [^J in three steps only
O
I!
(e) Ph - CH2 - C - CI » Ph - CH^ - CI
(Q Ph -C Hj -C l > Ph - CH2 - C - CI
(!§Bansal Classes Halogen Derivatives [19]
EXERCISE-III
Q.l A primary alkyl halide (X) C4H4Br reacted with alcoholic KOH to give (Y). (Y) reacts with HBr to give
(Z) an isomer of (X). On reacting with alkali metal such as sodium/dry ether gives (S) CgHj8 which was
differentfromthe compound produced when n-butylbromide was treated with Na. What (X), (Y), (Z)
and (S).
Q.2 On electrolysis
gives isocyanidean aqueous
test ethanoilcwith
and condenses solution of so
acetone todium
fromchloride
hypnoticgives
(Y). sweet
What smelling liquid
are (X) and (X). (X)
(Y)?
Q.3 The alkyl halide C4H9Br (A) reacts with alcoholic KOH and gives an alkene (B), which reacts with
bromide to give dibromide (C). (C) is transformed with KOH & sodamide to gas (D) which forms a
precipitate when passed through an ammonical silver nitrate solution. Give the structure formulae of the
compounds (A), (B), (C) and (D) and explain reactions involved.
Q.4 An unsaturated hydrocarbon (A) C6H10 readily gives (B) on treatment with NaNH2 in liquid NH3.
When (B) is allowed to react with 1 -chloropropane, a compound (C) is obtained. On partial hydrogenation
in the presence of Lindlar catalyst, (C) gives (D), C9H18. On ozonolysis (D) gives 2,2-dimethylpropanal
and 1 -butanal. Give structures of (A), (B), (C) and (D) with proper reasoning.
Q. 5 One mole of each bromoderivative (A) and NH3 react to give one mole of an organic compound (B).
(B) reacts with CH3I to give (C). Both (B) and (C) react with HN02 to give compounds (D) and (E),
respectively. (D) on oxidation and subsequent decarboxylation gives 2 -methoxy-2-methylpropane.
Give structures of (A) to (E) with proper reasoning.
Q.6 A chloro derivative (A) on treatment with zinc-copper couple gives a hydrcarbon with fivecarbon
atoms. When 'A' is dissolved in either and treated with sodium, 2,2,5,5-tetramethylhexane is obtained.
What is the original compound A?
Q.7 A primary alkyl halide (A) C4HjBr reacted with alcoholic KOH to give (B). (B) reacts with HBr to give
(C) an isomers of (A). (A) on reacting with sodium gives (D) CgHlg which was differentfromthe
compound produced when n-butylbromide was treated with Na. What are (A), (B), (C) and (D).
Q. 8 One mole ofa hydro carbon (A) reacts with 1 mole of bromine giving a dibromo compound C5HJ0Br2.
(A) on treatment with cold dilute alkaline KMn04 solution forms a compound C 5H1202. on ozonolysis
(A) gives edquimolar quantities of propanone and ethanal. Deduce structure of (A).
Q.9 A hydrocarbon (A) was found to contain 85.7% carbon and 14.3% H. This compound consumes 1
molar equivalent ofhydrogen to give a saturated hydrocarbon. 1 g of (A) just decolourised 3 8.05 of 5 %
solution by weight of Br2 in CC14. Compound (A) on oxidation with conc. KMn04 gave a compound
(C), C4HgO and (B) acetic acid. Compound (C) can easily be prepared by the action of acidic aqueous
mercuric sulphate on 2-butyne. Deduce (A), (B) and (C).
Q. 10 When a hydrocarbon (A) is treated with excess of hydrogen chloride, a dihalogen derivative (B) is
obtained. The compound (B) is treated separately with aqueous and alcoholic KOH to give compounds
(C) and (A) respectively both having three carbon atoms. Compound (C) does not reduce Tollen's
reagent and compound (A) give white precipitate with ammonical silver nitrate. Assign structures to
compounds (A) to (C).
EXERCISE-IV (A)
Q.l Chlorination oftoluene in the presence of light and heat followed by treatment with aqueous NaOH gives
(A)o-cresol (B)p-cresol
(C) 2,4-dihydroxytoluene (D) Benzoic acid [IIT 1990]
Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to
(A) The formation ofless stable carbonium ion (B) Resonance stabilization
(C) The inductive effect (D) sp2 hybridised carbon attached to the halogen
[IIT 1990]
, Qrf 1-Chlorobutane on reaction with alcoholic potash gives:
^ (A) 1-butene (B) 1-butanol (C)2-butene (D)2-butanol [ITT 1991]
The products of reaction of alcoholic AgN02 with ethyl bromide are [ITT 1991]
(A) Ethane (B) Ethyl nitrite (C) Nitroethane (D) Ethyl alcohol
Q.5 When nitrobenzene is treated with Br2 in presence ofFeBr3 the major product formed is:
m-bromonitrobenzene. Statements which are related obtain the m-isomer are
(A) The electron density on meta carbon is more than on ortho and para position
(B) The intermediate carbonium ion formed after initial attack of Br+ at the meta position is least
destabilized.
(C) Loss of aromaticity when Br+ attacks at the ortho and para position and not at meta position
+
(D) Easier loss of H to regain aromaticityfromthe meta position thanfromotho and para positions.
[ITT 1992]
Arrange the following compounds in order ofincreasing dipole moment

Toluene m-dichlorobenzene o-dichlorobenzene p-dichlorobenzene
I II III IV
(A) I < IV < II < III (B) IV<I <II <II I (C) IV< I<I II< II (D) IV<II<I<I II
[IIT 1996]
Q.7 In the reaction of p-chloro toluene with KNHj in liq. NH3, the major product is:
(A) o-toluidine (B) m-toluidine (C) p-toluidine (D)p-chloraniline
[IIT 1997]
<^8 (CH3)3CMgCl reaction with D 2 0 produces:
(A) (CH3)3CD (B)(CH3)3OD (C)(CD3)3CD (D) (CH3)3OD [IIT 1997]
Q.9 Benzyl chloride (CgHjCH^C^canbe preparedfromtoluene by cMorinationwith:

(A) S02CI, (B) SOClj (C)C12 (D)NaOCl [IIT 1998]
0.10 Toluene,
group when treated with Br / Fe, gives p-bromotoluene as the major product, because
2 the CH3
[IIT 1999]
(A) is para directing (B) is meta directing
(C) activates the ring by hyperconjugation (D) deactivates the ring
0Cfl The order ofreactivity ofthe following alkyl halides for a S ^ reaction is: [ITT 2000]
(A) RF > RC > R-Br > R-I (B) R-F > R-Br > R-Cl > R-I
(C) R-Cl > R-Br > RF > RI (D) R-I > RBr > R-Cl > R-F
A Identify the set of reagents / reaction conditions 'X' and 'Y in the following set of transformation:
Y
CH3 - CH2 - CH2Br x > Product > CH3 - CH - CH3
1
Br
(A) X = dilute aqueous NaOH, 20°C; Y= HB r / acetic acid, 20°C
(B) X = concentrated alcoholic NaOH, 80°C; Y=H Br / acetic acid 20°C
(C) X = dilute aqueous NaOH, 20°C; Y= Br 2 / CHC13,0°C
(D) X = concentrated alcoholic NaOH, 80°C; Y=Br2/CHC13,0°C [IIT 2002]
Q.13 CH3MgBr + Ethyl ester -» which can be formed as product, [IIT 2003]
(excess)
CH2CH3 CH,
(A) HO- -C H 2 CH 3 (B) HO- " CH2CH2CH3
CH2CH3 CH 2CH3
CHjCH^ CH3
(C) HO- (D) HO- —CH 3 '
CH, CH,
Match the following:

Column I Column II
(A) CH3-CHBr-CD3 on treatment with ale. KOH gives (P) El reaction
CH2:=CH-CD3 as a major product.
(B) Ph - CHBr - CH3 reacts faster than Ph-CHBr-CD3. (Q)E2 reaction
(C)gives
Ph-CHj-CHjBr
Ph-CD=CHon treatment with C2H50D/C2H50~ (R) El cb reaction
2 as the major product.
(D) PhC H^ f^ Br and PhCD2CH2Br react with same rate. (S) First order reaction
/
EXERCISE-IV (B)
Q.l Fill in the blanks:
(a) Butan nitrile can be prepared by heating _ with alcohalic KCN. [IIT 1992]
jvf Amongst three isomers of nitrophenol, the one that is least soluble in wateris_ [IIT 1992]
Q.2 Identify the major product in the following reactions: [IIT 1993]
CI
CgHj — CH2 — CH - CH 3 ? -> ?
KOH A
(ii) C6H5COOH + CH 3 Mg I - >9 + ?
Q.3 An alkyl halide X of formula CfiH]3Cl on treatment with potassium tertiary butoxide gives two isomeric
alkenes Y and Z (C6H12). Both alkenes on hydrogenation give 2,3-dimethylbutane. Predict the structures
ofX, YandZ. [IIT 1996]
Q. 4 Predict the structure of the intermediates/products in the following reaction sequence - [ET 1996]
Br
H-
MeO-
Ph
Q.5
I
- -— _AicohaiicKOH—^ BWrite structures of (A) and (B).
Heat
H1(excess)
(b) (CH3)2CHOCH3 > A+B Write structures ofAandB. [IIT 1998]
Heat
Q. 6 Complete the following reaction with appropriate structures of products/reagents. [DT1998]

CH=CH2
Br2 ^ (i)NaNH 2 (3equi.) ^ ^
(II)CH3I
Q.7 What would be major product? [IIT 2000]

CH,
I c H OH
CH 3 -C-CH„Br 2 5 >9
A
I "
CH 3
Q. 8 How would you synthesis 4 methoxyphenol from bromobenzene in NOT more thanfivesteps? State
clearly the reagents used in each step and show the structures of the intermediate compounds in your
synthetic scheme. [IIT 2001]
Q.9 An alkene A (C16H16) on ozonolysis give only one product B (C8HgO). Compound B onreaction with
NaOH/I2 yields sodium benzoate. Compound B reacts with KOH/NT^NF^ yielding a hydrocarbon C
(CgHj Q). Write the structure of compound B and C. Based on this information two isomeric structures
can be prepared for alkene A. Write their structures and identify the isomer which on catalytic
hydrogenation (t^/Pd-C) gives a racemic mixture. [IIT 2001]
Q.10 Give maj or products A, B, C and D in following reaction sequence. [IIT 2004]
C H 2 -C1
K C N
> / a \ (i )NaOEt/EtOH . r m H3Oe .
( A ) > ( B )
DMF (ii)PhCHO/A ' ^
c
(ii)CH3NH2I
2
V^v (i)SOCl
ANSWER KEY
EXERCISE-I (A)
Q. l D Q.2 A Q.3 C Q.4 D Q.5 A Q6 D Q7 A
Q.8 B Q9 C Q.10 C Q.ll C Q.12 C Q.13 A Q.14 D
Q.15 C Q.16 B Q.17 A Q.18 D Q.19 C Q.20 D Q.21 B
Q.22 C Q.23 D Q.2 4 C Q.25 D Q.26 B Q.27 B Q.28 A
Q.29 B Q.3 0 C Q.31 B Q.32 B Q.33 C Q.34 C Q.35 A
Q. 36 A Q.37 C Q.38 C Q.3 9 A Q.40 B Q.41 A Q.42 A
Q.43 A Q.44 B Q.45 A Q.46 D Q.47 B Q.48 A Q 49 C
Q.50 B
EXERCISE-I (B)
Q.l D Q.2 A,C Q.3 B,C Q.4 A,B
Q5 A,C,D Q.6 A,B,C, P Q.7 B Q.8 A,B,D
Q9 B,C,D Q.10 B,D Q.ll A,D Q.12 A,C,D
Q.13 A,C,D Q.14 A,C,D Q.15 B,D Q.16 A,B,C,D
Q.17 A,B Q.18 A,B,C Q.19 A,B Q.20 A,B,C
Q.21 A,C Q.22 B,C Q.23 A,B,C,D Q.24 B,C,D
Q.25 A 3, B 2 ,C 1,D —> 2 Q.26 A -> 4, B 3,4, C - > 3, D -> 1,2
Q.27 A—>2, B—>•!, C—>4, D - » 3 Q.28 ( A ) - S ; ( B ) - - Q; ( C ) - R ; ( D ) - P
Q.29 ( A ) - Q ; ( B ) - S ; ( C ) - R; (D) - P Q.30 (A)-Q;(B)- - R ; ( C ) - P ; ( D ) - Q
EXERCISE-II
Q. l (i) CH 3 - CH - CH,, attack take place on less stericaUy carbon

I
OH
Q.4 (ii)
Q-5 (A)\TSJ
H
Me Me Me
I I I
(c) (A) Me - C = CH - Me, (B) Me - C - C H 2 -Me, (C) Me-C-CH 2 Me
OEt I
(d)(A) n , (B) | 0 | ,(c) | O j

1 1
Me
-
OTs
Me H Me Br
x OH OH
\ Et ° | ^CH2-CH2-OH
Q.6 (b) Ph-C-<^> (c) Et-CH-Et
o
(e)
N
Q.7 (d) Q.8 N
H
Q.9 A= O L - C H - C H = CH9 Bs C - C - C = C-C1

I I
CH3 C
Conversion (l)NaNH2 (2) H^/Pd BaS04
Q.10 (a) & (c)
CH3
I
Q .ll (a )As Et-I (b) B = CH3 - CH - OH (c) Me2C=CH2
OH
I
(d) Me2C=CH2 (e) Me-CH-CH2 & Me - OH - CH2
OH
Q.12 The mechanism of

® C1CH2CH2CH2CN (ii) PhCHF2
(iii) FCH2CH = CHC02Me (iv) Efl
(v) no reaction
Q.13 (i) Chloroform responds carbylamine test while ethyl alcohol does not. Carbylamine test- The compound
is heated with aniline and alcoholic caustic potash-an obnoxious smell of phenyl isocyanide (C6H5NC)
is produced.
(ii) Chlorine atoms of chloroform can be easily replaced by - OH group s on treatment with NaOH. Hence
chlorine atoms come in the form of sodium chloride. The solution thus when treated with silver nitrate
solution gives white precipitate of silver chloride. Chlorine atom in vinyl chloride is not readily replaced
by NaOH, hence it does not give precipiatet with AgN0 3 solution.
(iii) The two compounds are hydrolysed with aqueous NaOH when 1,1 -dibromoethane form acetaldehyde
while 1,2-dibromoethane gives glycol.
(iv) Chlorine atom in chlorobenzene is very less reactive, while chlorine in cyclohexyl chloride is very reactive.
Hence the two can be differentiated as above in (ii)
(v) Apply test (ii) as above; when benzyl chloride gives white precipitate with AgN0 3 solution, while O
chlorotoluene does not give precipitate. Alternately, the compounds are oxidised when o chlorotoluene
give o-chlorobenzoic acid when benzyl chloride gives benzoic acid (having non chlorine.)
(vi) n - Hexane does not respond CI" ion test even after fusion with Na and treatment with acidic AgN03.
the remaining three compounds are distinguished by their reactivity with alcoholic AgN03 solution.
(a) CH3 -CH= CHC 1 (a

(b) CH, = CHCHjCl (an
(c) cHravcivci
Q.14 The elimination ofHI (or DI)

involves breaking up of C - H (or C-D)
elimination is faster in case of CH3 - CH,I.
Q.15 H3C-CH-CH-CH3 KQHW > C H 3 -C = CH -C H 3 + C H 3 -C H - CH = CH2
CH3 CI CH 3 ch3
shydrogenated carbon.
s with I 2 to give PI3 a

> + 3 I 2- > 2 P I3
t OH + PI3 3RI + H 3 P0 3
Q.21 KCN is an ionic compound [K+(:C =N:)-] in which both C and N carry a 1
to give alkyl cyanide AgCN
N atom and R-N = Cis
faBansalCl
Q.22 The strong - 1. E offluorineatom in F3C - C < produces partial +ve charge on C atom of CF3 which
ultimately increases+ve charge on 2nd carbon atom to destabilize it
F
t +5
i
F
In F3C+, the unshared pair ofelectrons in the p orbitals ofeach of thefluorineatom are shifted to C+ via
p-p orbital overlapping and thus stablizing F3C+ ion
Q.23 Dry gaseous hydro halogen acids are better electrophile. Also in aqueous solution FÔ acting as nucleophile
may produce alcohol.
Q.24 KI reacts with RC1 to form RI. This RI molecule now hydrolysed easily to give ROH because alkyl
iodide are more reactive than alkyl chloride.
H 0H
RC1 + KI -» RI • > ROH (more fast)
Q.25 The more pronounced the nucleophilic activity ofthe attacking reagent, then the more the SN2mechasnism
will be favoured. Since in SN1 mechanism the raegent doesnot enter into the rate determining step of
ionisation How ever it can also be expected that as the nucleophilic activtiy is so slow that the mechanism
will changefromSN2 to SN1
Q.26 The dielectric constant ofwater is greater than that of aqueous acetone, and so ionisation of benzyl
chloride is facilitated.
Q.27 On movingfrom3° to 1 ° alcohol rate of ^ 2 reaction decreases and reaches to minimum and mechanesm
changesfromSN2 to SN1, Then rate of SN1 rate of reaction increases.
Q.28 Anhydrous A1C13 is used as a catalyst infriedelcrafts alkylation.
Q.29 tert-Butyl chloride, sec butyl chloride and CC14 with ale. silver nitrate
Me3C - CI > ">CHC1>CC1 4

c2H^
Br
Q.30 (a)As Q C ^ j] D. Q f
CuLi
-10 2 Hs
Q
1=
o
faBansal Classes NOMENCLATURE OFORGANIC COMPOUND [28]
Me Me
(b) (A) EtO Pr, (B) Pr EtO
H H
e ©
Q.31 A = CjqH jj- C^CH B e C10H21-C^CLi C - C- C - C- C - C- B r
C
D = C 1Q H 21 - C = C - ( C H2 ) 4 - CH - CH 3 E e C 1q H 21 - C = C - ( C H 2 ) 4 - C H - C H .
CH H H CH
CH
F-C10H21-C-C-(CH2)4-CH-CH3
H 0 H
Q.32 (i)A,CH 3 CH 2 CH 2 Br;B, CH 3 CH = CH 2 ; C, CH 3 CHBrCH 3 ; D, CHgCHNE^CHg

(ii) A, CH 3 CH = CH ^ B, CH 3 CHOHCH 3 ; C, CH 3CHC1CH3; D, CH 3 CH 2 CH 2
(iii) A, CH 3 CHBrCH = CIi 2 ; B, CH2=CH-CH=CH2; C, CH 3 CHBrCH=CH2 & CH 3 C H = C H - C ^ B r
(iv) A, CH 3 Clr^CHOHCH 3 ; B, CH 3 CH 2 CHBrCH 3 ; C, CH 3 CH = CH - CH 3
EXER CISE-III
Br
Q.L C H 3 - C H - C H 2 -CI C H 3 - C = CH 2 CH 3 -C-CH
CH. CH 3
(X) 2 - Bromo - 2 - methyl propane
(Z) (isomer of X)
(C H 3 ) 2 CH — C H 2 -CH 2 -CH (CH3).
(2,5 - dimethyl Hexane)
(S)
Q.2 (Y)
Chloretone (Hypnotic)
Q.3 CH 3 CH 2 CH 2 CH 2 Br CH 3 CH 2 CH = CH, CH , — CH , — CH — CH,
Br Br
(A) (B) (C)
CH 3 - CH2- C = CH
<P)
<!SBansal Classes Halogen Derivatives [29]
Q.4 (CH 3 ) 3 C - C 3 CH (CH 3 ) 3 C - C =C"Na + (CH3)3C-C = CH ^^ C T^

(A) (b) (C)
(CH 3 ) 3 C - C H = CHCH2 CH2CH 3

(D)
OC H 3 OC H 3
I CH 3 - C(CH 3 ) - CH 2 - CH 2 NH 2
Q.5 C H 3 - C ( C H 3 ) - C H 2 - C H 2 -Br
(B)
(A)
OC H 3
OC H 3
CH 3 - C(CH 3 ) - CH 2 CH 2 - NHCH 3 CH 3 - C(CH 3 ) - CH 2 CH 2 - OH
(C) (D)
OCH,
CH3-CH-CH2-CH2-N-N = O
CH,
(E)
Q.6 (CH 3 ) 3 C - C^ CL
CH 3 CH, CH,
I
C H 3 - C = CH H 3 C — C — CH 3
Q.7 CH 3 - C H - C H 2 B r Br
(B) (Q
CH,
(A)
CH,
CH 3 - CH - CH 2 CH 2 - CH - CH 3
(D)
CH, ^CH,
Q.8
C=C
CH, "H
(A)
CH 3 CH 2
CH^ CH2
Q.9 C = CH - CH , CH 3 -COOH ;c = o
X
CH 3
CH,
(A) (B) (Q
CI
Q.10 CH3- C = CH
CI
(A) (B) (C)
Q.ll CH 3 -(CH 2 ) 3 C-C1 CH3(CH2)2CH = C(CH3)3

I
CH3
(A) (B)
Q.12 H 3 C-CHX 2 (X = Halogen)
Q.13 (CH 3)2 CH-CHCH2 CH 3 (CH3)2CH CH = CH CH3

CH3.^ C =C
.C2H5
(A) (B) (C)
Q 14 (A) CHGCE^CTYBR, (B) C H ^ H ^ O H , (C) CH GC H^ C^ OC^ C^ C^ , (D) CHJ-CH-CH^

(E)CH3CH(OH)CH3
Q. 15 (X) C2H4C12, (Y) CI - CHjCHJ - CI, (Z) CH3CH
Q.16 HC^C-CH^Cl
EXERCISE-IV (A)
Q.l D Q.2 D Q.3 A Q.4 C Q.5 A,B Q.6 B Q.7 B

Q.8 A Q.9 A,C Q.10 A,C Q.ll D Q.12 B Q.13 D
Q.14 A- Q; B - Q; C - R,S; D - P,S
EXERCISE-IV (B)
Q.l (a) propyl chloride, (b) ortho
Br
Q.2 (i) C 6 H 5 -CH = CH-CH3 ; C 6 H 5 -CH-CH 2 -CH 3

(ii) C6H5COOMgI + CH4
ch3 ch3 ch3 ch3
Q.3 (X):CH 3 -C — CH-C H 3 ;(Y): CH 2 =C —CH-CH 3 ;(Z): CH 3 -C —CH-CH
CI ch3 ch3
H- -Ph
Q.4 MeO- - H (NGP due to MeO, so retention of configuration)
Ph
CH 3
Q.5 (a) Cis and trans forms of stibene C6H5CH=CHC6H5; (b) ^>CH1 + CH31
Cri-j
h
Br
C=CNa G=CCH3
,CH-CH 2 Br
Q.6 (A)fQ NaNH,(liq.) CH-J *(B)
CH,
Q.7 CH 3 -C-CH 2 CH 3
oc2h5
Br ONa
ONa OMe OMe OMe OMe
NaOH
conc.H,SOd NaOH
^ I C3J A high pressure^ [ o ) MejSO^ [ o ] ' -Co)- -> (0 )
SO,H ONa OH
Alternative rout
Br Br OMe OMe
Br Br
naoh n a o h
o j - ^ ^ i o j > [ q j ^ l o j - . . _ > [ o j - ^ l q .
OMe ONa OH
SOiH ONa
z H KOH
KU
Q.9 (A) PhC(Me)=C(Me)Ph °r "- 3° > (B) 2PhC - Me N H 3 - N"H 3 > (C) PhCH2Me
Two isomers ofA are cis and trans
CONHCH,
!
CN COOH CH = C
Q.10 (A) (D) [OJ LOj
mBansal Classes Halogen Derivatives [32]
Q.13 Which is incorrect about Hunsdicker reaction?

(A) Only Cl2 can give alkyl halide
(B) I2 will give ester when treated with RCOOAg
(C) The reaction proceeds through free radical
(D) F2 cannot give alkyl halide
Q.14 Major product for the reaction

o c h ->is:
Br
(A) Br
Br
(C) (D)
Br
Me Me Me
f5 HO—|—H — H—| —CI — -> H- -OH
Et 11 Et 1 Et
B A
Steps I and II are
(A) both SN1 (B) both SN2 (C) ISN1, II SN2 (D) I SN2, IIS N 1
Q.16 What are A & B in the following reaction?
CI
Mg/THF . (i)CH3CHO ^
J\. f Jj
.^ -B r (ii)aq.NH4Cl
MgCl CHOHCH3 CI CI
(A)
Br
*{S V ^-Br
(B)
MgBr
&
CHOHCHi
MgCl MgCl
(C)f| & (D) None of these

Br ^-CHOHCH3
H, 0 +
Q.17 Ester A (C 4 H 8 0 2 ) + CH3MgBr > C4H10O
(2 pair) (alcohol)
(B)
Alcohol B reacts fastest with Lucas reagent. Hence A and B are
O O
(A) CH3 - C - O - C 2 H 5 , (CH3 )3 COH (B) H - C - O - C 3 H 7 , (CH, ) 2 CHOH
O o
II II
(C) CH 3 - C - 0 - C 2 H 5 , ( C H 3 ) 2 CH 0H (D) H- C- O-C 3 H 7 , ( C H 3 ) 3 COH
faBans al Classes NOMENCLATURE OFORGANIC COMPOUND [3]
Q.18 The hydrolysis of alkyl isocyanides (R-CH2-N C) gives

(A) RNHCOOH (B) R - CH - COOH (C) RNH2 + HCOOH (D) RCH2NH2 + HCOOH
NH2
What is product of the following reaction?
•CI Mg
?
CI ET,0
Qc
MgCi CI
(D) None of these
(A) (B) MgBr (Q
Following reaction is:

\JX*
H H
CH 3(CH 2)5^ 1 i .(CH2)5CH3
X-Br HO-C
H,C' ^CH3
(A) SE2 (B) SN1 (C) SN° (D) SN2
B r C H 3
1 V~V OH-
V^
H A _ A H
Ais:
HOV / Y ,C H 3 H\/ \/ 3
(A)
h/LAH (B)
oh/V_AH
(C) Both (D) None
CHCI3 + OH- » HCOO"
Intermediates of this reaction are
(A) :cci: (B) :CCL (C) both (D) None
3 Racemic mixture is obtained due to halogenation of:

J&
(A)n-pentane (B) Isopentane (C) neopentane (D)BothA&B
For CH3Br + OH" > CH3OH + Br
the rate of reaction is given by the expression:
Q.24 (A) rate = k [CH3Br] (B) rate = k[OH"]
_
(C) rate = k [CH3Br][OH ] (D) rate = k[CH3Br]° [OH"]°
Which will give white ppt. with AgN03?
Q.25 (A) \ )—CI (B) ( O V - C I (C) ( O / ~

c h
2
c i
(D) Both A & C
The reaction of SOCl2 on alkanols to form alkyl chlorides gives good yields because
(A) Alkyl chlorides are immscible with SOCl2
(B) The other products ofthe reaction are gaseous and escape out
(C) Alcohol and SOCI2 are soluble in water
(D) The reaction does not occurs via intermediate formation of an alkyl chloro sulphite
[194]
<!§Bansal Classes Halogen Derivatives
Q.27 True about alkyl halides is/are:

(A) Tertiary alkyl halides undergo £^2 substitutions
(B) Alkyl iodides on exposure to sunlight gradually darken
(C) Alkyl chlorides do not give beilstein test
(D) A nucleophilic substitution is most difficult in alkyl iodides
Q.28 The product formed when glycerol reacts with PC15 is-
(A) 1,2,3-trichloropropane (B) Glycero monochlorohydrin
(C) Glycero dichlorohydrin (D) All of these
Q.29 On heating glycerol with excess amount to HI, the product formed is-
(A)Allyl iodide (B) Isopropyl iodide (C) Propylene (D) 1,2,3-tri-iodopropane
To prepare 3-ethyl-3-pentanol the reagents needed are:
(A) CHgCHjMgBr + CH,-C- CH2CH3
Ii
0
(B) CH3MgBr + CH3CH2 - C - CH2CH3

II
O
(C) CH3CH2MgBr + CH3CH2 - C - CH2 - CH3
II
0
(D) CHgCHjCT^MgBr + CH3 - C- CH2CH3
II
O
Non-occurence ofthe following reaction
Br + CH3OH > BrCH3 + OH , is due to
(A) Attacking nucleophile is stronger one (B) Leaving group is a strong base
(C) Alcohols are not good substrate (D) Hydroxide ions are weak bases
\_J^32 When ethyl bromide is treated with moist AgjO, main product is:
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All ofthe above
yJJ^f When ethyl bromide is treated with dry Ag ^, main product is:
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All ofthe above
CH,
H- D c H O-
Q.34 H_ Br — — > ? Major product is:
C2H5OH
CH
h 3 C x /H H3Cv /CH 3
(A) (B) > <
H3Cx ^ch3 H3Cx ^H

C = C
(C) (D) / \
X
IK ^D D CH3
<!§Bansal Classes Halogen Derivatives [5]
Q35
(A) u O (B) La J (C) both (A) & (B) (D),

H —- A CH 3
Q.36 BR——H
E2
(A) S (B) S (C) JJ (D) None is <
S ) E ^ ^ n e 0 S 8 e n e Ê Ay lcWoT de (C) Ethyl alcohol (D)]
(A) CH3CHO and PC15 (B) CH3COCH3 and PC15

(C) CHj = CH2 and tij (D) CF^ = CHC1 and HCl
Agp<nvder H s0
Q.39 CH3 - C - CH3 - i s > (A) > (B) * * > Product A, B&Ci
il -
(A)]
(C)]
Q.40
3
^
r^T
rrt
izt
ir™
(C)Alkanols ofthe structure CH3CH(OH) - R (where R = H, alkyl or aryl) give i
(D)'
Q.41 A
042
( A ) Q C B ) |£ ) ( C ) ^ .(D) I
— —
Q. 43 The appropriate naming for the second step in the haloform reaction is:
(A) Halogenation (B) Dehydrohalogenation
(C) Reduction (D) Dehydrogenation
Q. 44 Which product is obtained when bleaching powder is distilled with acetone:

(A) CC14 (B) CHClg (C) CH2C12 (D) CH3C1
Q.45 What will be the reduction product of following reactions:

+2H
Zn/HCl (ale)
+4H
CHCI3-
Zn/HCJ (aq.)
+6H
Zn/H2 0
(A) C H ^ , CH3CI, CH4 (B) CH4, CH3CI, C H ^

(C) CH3CI, CH ^ , CH4 (D) CH3CI, CH4, CF^Cl
Q.46 Fe/HCl reduction of 'pyrene'(CCl4) gives:

(A) CH4 (B)CH2C12 (C) CHoCl (D)CHC13
Q. 47 Addition ofbromine on propene in the presence of brine yields a mixture of:

(A) CH3CHClCH2Br and CH^CHBrCI^Cl (B) CH^CHClCF^Br and CH3CHBrCH2Br
(C) CH3CHC1CH2C1 andCT^CHBrCHjBr(D) C^CHCIC^CI and CH3CHBrCH2Cl
3
0 /^Y™
Q.48 is converted into I by:
+
(A) (i) CH3~ Mgl, H30 (ii) H2S04, A, (lii) HBr, R202
+
(B) (i) CH3- Mgl, H30+ (ii) H2S04, A, (iii) HBr
(C) (i) CH3-MgI, H 30 (ii) HBr
+
(D) (i) HBr, R ^ (ii) CH3-MgI, H30
Q. 49 To form Malonic acid, by shortest possible route, we have to start a reaction from:
(A) Ethyledine chloride (B) Methyl chloride (C) Methylene chloride (D) Chloro ethan
Q. 5 0 Frankland reagent is:

(A) Dialkyl lithium (B) Dialkyl Zinc (C)Dialkyl magnesium (D) Dialkyl aluminium
[197]
<!§Bansal Classes Halogen Derivatives
EXERCISE-I (B)
(Choose the correct option. One or more than one are correct)
Q.l In the given reaction:

H
[X]is:
H
H
Br
( A ) k X J ( B ) r N 1 (C) (D)
Br
Br
Q.2 Consider the following statements?

(A) CHJ-CH J-CH J-I will react more readily than (CH 3)2 CHI for S N2 reactions.
(B) CH3-CH2-CH2-C1 will react more readily than CT^-Cf^-CHj-Br for S N2 reaction.
(C) CH 3 -CH 2 - CH 2 -C H 2 -Br will react more readily than ( C H ^ C - C I ^ - B r for SN2 reactions
(D) CH 3 -0-C 6 H 5 -B r will react more readily than N0 2 -C 6 H 5 -C H 2 Br for SN2 reaction
Q.3 A solution of (R)-2-iodobutane, [a] = -15.9° in acetone is treated with radioactive iodied, until 1.0% of
iodobutane contain radioactive iodine, the specific rotation of recovered iodobutane is found to be
15.58°, which statement is correct about above information.
(A) It has optical purity 96% (B) % of R in solution is 99%
(C) Racemic mixture is 2% (D) Final solution is dextrorotatory
Q. 4 Which are possible products in following
CH 3 . A „
moistAg,U
2
CH 2 CI —>
CH 2 OH CH 2 OH CH
£
CH, „ ^ ^ X
Xchoh <&< 1 (C)C > (D)
OH
Q.5 In which product formation takes place according to Hoffinann's rule
t e® 0®
(A) CH 3 CH 2 - CH - CH 3 "B^0K > (B) CH 3 CH 2 - CH - CH 3 CH C
3 ÔK >
Br Br
CH 3
&/ ©
o h
e
011
(C) CH 3 CH 2 -CH-N CH 3 > (D) CH CH C H - C H >
CH, CH, S
S(CH3 V
(i)Et2 H2Cr 4
Q.6 A+B ° > Alcohol ° > Ketone
CH
(C)Bis CH3-CHCOCI (D) Ais isopropyl magnesium iodide
H
CH
Q.7
I
H
CH 3 CH 3
(A) CH 3 - C H - C H 2 B r (B) CH3 - CBr - CH.
Br
(C) CH3CH 2CH 2Br (D) CH 3 - C H - C H•33
Q. 8 Select the correct statementsfromfollowing
(A) CH3 CH2CH2I will react more readily than (CH3)2CHI for
(B) CH3CH2CH2C1 will react more readily than C ^CH jC HjB r for
(C) CH3CH 2CH2CH2Br will react more readily than (C H ^C H- CI ^B r for
(D) CH 3 -0-C 6 H 4 -C H 2 Br will react more readily than N0 2 -C 6 H 4 -C H 2 Br for S.
Q. 9 Which of the following will react with AcO Ag
(A)R-NH2 (B)R-OTs (C)R-N 3 (D)R-Br
Q.10 Consider the given reaction
H -C -O T S NaCN
CH 3CH 2CH-CN
which of following statements are correct for above reaction.

(A) Product formation takes place due to the breaking of O-Ts
(B) The reaction is Sn2
(C) The reaction is Sn1

(D) Configuration ofproduct is (R)
Q.ll Benzoyl chloride is less reactive than acetyl chloride for nucleophilic acyl substitution reaction because
0
(A) - C - group ofbenzoyl chloride is in conjugation with benzene ring. This makes benzoyl chloride
more stable than acylchloride.
(B) CH3- group of acetyl chloride make C-Cl bond stronger due to the +1 effect.
(C) C6H5- group ofbenzoyl chloride make C-Cl bond weaker due to +R effect.
(D) Carbonyl carbon in benzoyl chloride is less electron deficient than acetyl chloride
Q.12 Bromination can take place at
(A)L (B)5 (C)3 (D)4
Q.13 Which offollowing will give syn-elimination

(A) CH3CH2CH2-OCOCH3 (B) CH3CH2CH-CH3
CI
IsI CH3
Q.14 Which offollowing are correct for given reaction
N-ÔH
(A) Major product ofreaction is
A
(B) Major product is
(C) The reaction is thermal elimination reaction

(D) The reaction is cyclic E2 reaction
Q .15 Haloform reaction is given by

(A) All 2° alcohol (B) All methyl ketones
(C) All the compounds having CH , - C - group (D) Chloral
Q .16 Identify the compounds that will undergo NGP reaction

(A) CHjCHj-S-CHjCHjBr (B) CH3-NtICH2CH2CH2Br
(C) C H 3 - C H - C = O (D) CHg-O-CH^CI^CI^Br
I le
Br O0
Q .17 Which alkyl halide undergo E2 elimination

Br
CMe3
(A) (B)
CMe, CMe,
(C) <P)
Br
Q.18 3-Phenyl-3-pentanol can be prepared from grignard reagent & other component which can be
(A) 3 -pentanone (B) Ethylbenzoate (C) Ethyl phenyl ketone (D) Propanoyl chloride
Q.19 In which of following reaction inverted product will obtained.
(A) SN1 (B)Sn2 (QSnN gp (D)V
Q.20 Rate ofSN2 will be negligible in

Br Br Br Br
(A) (B) (C)

0> "0
Q.21 SN1 & SN2 is not favourable in

(A) HJC = CH-C1 (B) Ph-CHJ-Cl (C) Ph-Cl ( D) H^CH- CI VCL
Q.22 SN1 & SN2 product are same in (excluding stereoisomer)
(A) (B) (Q (D) Ph - CH - CH - CH 3
a
CH 3 CI
Q.23 Rate ofS N 2 depends on

(A) Cone of Nucleophile (B) Cone of substrate
(C) Nature of leaving group (D) Nature of solvent
Q.24 CT NaOI ) yellnw solid

G can be
( A ) C H3 - C - O C H3 (B) C H 3 - C - C H 2 - C " C H 3
II
O O O
(C) CD3COH (D) C—CH3

o
Q.25 Match the List I (reaction) withList II (reaction intermediate) and select the correct answer using the
codes given below the Lists.
List I Listn
(A) CF3-CHC12 alc.KOH/A > CF2 = CC12 (1) Transition state
CH 3
(B) CH3 - C - OH > CH, - C = CH, (2) Carbocation
~~
CH,
CH,
al cK O H
(C) CH3-CH2-Br > CH 2 -CH 2 (3) Carbanion
Br
(D) CH 3 - C - CH 3 aq.KOH/A > ^ ^ ^ (4) Free radical
CH, CH,
^Bansal Classes Halogen Derivatives P2J
Q.26 Match the List I with List II and select the correct answer using the codes given below the Lists.
List I Listn
(A)E1CB (1) Quaternery Amine oxide
(B) Saytzeff alkene as major product (2) Xanthate
CI
(C)E2 (3) CH 3- CH 2 - C H - C H3
(D)EC (4) C6H5-CH2-CH-CH3
Q.27 Match List I with List II and select the correct answer from the codes given below:
Lis tI List II
(A) CH 3 -O-SO 2 CH 3 + C 2 H 5 O (1) CH3—CI^—PH 2

(B) CH 3 -CH2-I + PH 3 (2) CH 3 -O-C 2 H 5
Q 0
(C) HC = CNa + CH 3 -CH2-Br (3) CH 3 -O-CH 3
(D) CH 3 -CI + CH 3 -O (4) CH=C-CH 2 -C H 3
Q.28 Match List-I with List-II for given S n 2 reaction & select the correct answer from the codes given below
Z-CHJBR + CH 3 0 • Z-CH 2 -OCH 3 + Br

List-I List -n iftcdl'i
(A)H- (P)0.1
(B) CH 3 -
(0)3
(C)C 2 H S -
CH 3 R)l
(D) \ CH—
CH / (S)100
Q.29 Match List-I & List-II and select correct answer

List-I List -n
H,O
(A) R-M gX + HCHO > Adduct
n-carbon (P) Ketone
(B)R-MgX + (CH2) 2 0 • Adduct >

n-carbon (Q) 1° Alcohol (n+ 1) carbon
H3
( C ) R - M g X +C 0 2 • Adduct ° >
n-carbon (R) Acid (n + 1) carbon
h
(D) R-M gX + Ph-C=N - • Adduct 3° >
(S) 1 0 Alcohol (n + 2) carbon
Q. 30 Mat ch the follow ing

List -n
List-I
/OCH 3
W-
-C>
CH,0 CH,CH 2 Q >
(P)E1
(A)
CH,0
CH3O
0
II
c
CH 3 CH 2 O
(Q) E2
CB)
W
CH33 CH22CH2Br
CH,CH,OD
(R) Elc b
(C)
o o
Br
Br
ale. KOH (S)Ec
CD)
Halogen Derivatives [14]

feBansal Classes
EXERCISE-II
Q.l Explain the following giving proper resoning:
(i) Treatment of 1,1 -dimethyl oxirane with sodium methoxide in methanol gives primarily one product. Also
identify the product giving its IUPAC name
(ii) Trimethyl amine reacts with alkyl iodide (RI). As the reaction proceeds the reaction rate abnormally
increases, inspite ofdepleting concentration of reactants.
(iii) Optically active 2-iodo butane on treatment with NaI*/Acetone gives a product which do not show
optical activity. —
(iv) In the solvent DMSO the order of reactivity ofhalide ions with methyl bromide is F~ > Cl > Br" > I~
opposite to that observed in methanol solution.
(a) (n - C3H7)3N + CH3I -»(n - C3H7)3NCH3+
Relative rate: in hexane, 1; in chloroform, 13000
(b) Br - + CH3OTs-»CH3Br + TsO-
Relative rates: in methanol, 1; in HMPT, 105.
(v) Although ethers are weakly polar, are used as solvent of choice for Grignard reagents.
(vii) Treatment of either CH3-CH - CH-CHjBr or CH3-CH -CH - CH2 with aqueous HO~ gives the
O O
same product. Also write down mechanism involved, & IUPAC name ofproduct.
Q.2 On reaction between an alkyl halide and KOH in a mixture ofwater and ethanol, compare the two
mechanisms SNj and SN2:
(a) relative rates of CH3X,C2H5X,iso-C3H7X&tert-C4H9X
(b) relative rates for RC1, RBr and RI
(c) effect on rate of a rise in temperature
(d) effect on rate of increasing water content ofthe solvent.
(e) effect on rate increasing alcohol content ofthe solvent.
Q.3 In the following reaction is carried out in the weakly ionizing solvent, acetone (CH3)2C=0. (Bsisbrosyl,
p-bromo benzene sulfonyl)
n-C4H9OBs + X - >n-C4H9X + BsO-
The order ofreactivity ofhalide ions depends or the salt used on their source :
ifLi+X~ isused,I—^r-^Cl-
if (n-C4H))4N+ X - is used Cl -> Br -> I~
How do you account for this contrast in behavior ?
Q.4 Which of the following is the correct method for synthesizing 4,4-dimethyl-pent-2-yne, using sodamide
in liquid NH3? Given reasons.
CH3 CH3
(i) CH3C=CH + CH3 - C - Br > (ii) CH3 - C - C = CH + CH3I — >
CH3 CH3
Q.5 Give the products andfindall unknowns.
A
(a) I^N CH2 CH; CH, C ^ Br >
C 2H 5O
CH3
C2H 5OH
(b) CH3-C-CH2-Br
CH3 Nal
H H TsCl * NaBr
(C) n Pyridine
v
A B
CH, OH
Q.6 Find out the unknown alphabets.
H3 +
(a) 'CH3 + CH3CH2MgBr(l eq) ° > A
MgCl
(b) Ph-€OCl + B
o
(2 eq)
O
(c) H - C -O Et + CHgCHjMgBr h3o+ ? c

(2 eq)
MgI
(d) QC + D
(1 eq.)
CH2
HCl
(e) •> E
H3C Ph
C 2 H5
Q.7 To prepare <J>-C-C2H5 by RMgX which is the incorrect pair

OH H,0
(a) <J)MgBr + (C2H5)2CO
(b) C2H5MgBr + ^>C =0 >

H C
5 2
H
(c) C2HsMgBr + <j>-COOCH3 z° >
H2
(d) <f>MgBr + C 2H5COOCH3 ° >
I
H
Ci
Zn .
I Zndust' A —n
Q9 CH 3 -CH-CH H -- C
CHH 2, -- C
C 1I -- c on ve r t?
B
CH3
Q.10 What is/are the limitation in the formation of Grignard reagent by RX+ Mg —dryether >
(a) R should not contain any acidic group
(b) R should not contain any electronegative group
(c) Alkyl halide should not be vicinal dihalide
(d) Alkyl halide can't be Tertiary.
Q. ll Identify the unknowns
(a) CH^jCHjCl + 1 ~ - » A
(b) (CH3)2CH-Br + KOH (aq.) —» B
(c) (CH3)3C-Br + KCN (ale.) -> C
(d) (CH3)3C-Br + KOH (aq.) -> D
CI
Conc NaUH
® CH 3 -CH-CH 2 -OH ) E,
Q.12 Write major product ofthe the following reactions:
0) C l C ^ O ^ C H ^ r + KCN ™ >A
SF
(ii) PhCHO * >B
Oii) BrCH2CH = CHC0 2 Me ^ >C

(iv) EtOH + HI >D
(v) EtOH + HCN >E
Q.13 State at least one characteristic test which can distinguish:

© C 2 H J OH from CHC1 3
(ii) Halogen atoms present in CHC13 and CH2 = CHC1
(iii) 1,1- dibromoethane from 1,2-Dibromethane
(iv) Chlorobenzenefromchlorocyclohexane
(v) o-Chlorotoluenefrombenzyl chloride
(vi) n-Hexane, CH3CH = CHC1, CH2= CHCH2C1 and O ^ O ^ CI ^ C l
Q 14 CH 3-CH 2I reacts more rapidly with strong base in comparison to CD-^CIÎ
Q. 15 2-chloro-3-methylbutane on treatment with alcohoilc potash gives 2-methylbutene-2 as major product.
Q.16 Iodoform gives precipitate with AgN03 on heating while CHC13 does not.
Q.17 Hydrogen atom ofchloroform is definately acidic, but that of methane is not.
Q.18 A small amount ofalcohol is added to chloroform bottles.
Q. 19 Treatment of Me3CCH = CH2 and Me3CCHOHMe with concentrated hydrochloric acid gives the
same two isomeric alkyl chlorides what are these two products.
Q.20 Iodine reacts with alcohols to give alkyl iodine only in presence of phosphorous.
Q.21 KCN reacts with R - 1 to give alkyl cyanide, while AgCN results in isocyanide as major product.
+
Q.22 The carbocation F 3 C - C < is unstable whereas carbocation F3C ismore stable.
Q. 23 Dry gaseous hydro halogen acid and not their aqueous solutions are used to prepare alkyl halides from
alkenes.
Q. 24 RC1 is hydroly sed to ROH slowly but reaction fastens on addition of KI.
+ + -
Q.25 The mechanism of decomposition of Me3 S OH" is SN2 whereas of Me 3S 1 is SN1.
Q. 26 Alkaline hydrolysis ofbenzyl chloride in 50% aqueous acetone proceeds by both ^ 2 and S^l mechanism,
when water is used as solvent, mechanism was now mainly SN1.
Q. 27 Ethanol is less reactive than methanol as well as isopropyl alcohols when treated with dry HCl gas.
Q.28 Anhydrous A1C13 is used as a catalyst infriedelcrafts alkylation.
Q.29 Arrange following compounds according to their reactivity with ale silver nitrate.
t-Butyl chloride, sec butyl chloride and CCL.
Q.30
(a) [ > CH? - OH - ^ A - ^ B

J.IMID4
C
+B NB S
^ q)Li a ^ » r 1 C ale.KOH.
(ii) CuF
CH,
(b) CH3CH2CH2 OH
(i)TsCl + Hi) K
kii)C2HsO"K kii)C2H5OTs
(A) (B)
What are (A) and (B) explain giving their stereochemistry.

TARGET IIT JEE 2007
[ORGANIC CHEMISTRY
XII (ALL)
HYDROC RBON
REACTION CHART FOR ALKANES
GMP GR
H2,Ni ) X , , hv or UV light or 400 °C
(1) R-OCH 200~300°C
(1) »RX
or
R-CHCH, Sabatier senderen^
(2) Nit rat ion R-N
reaction
Zn-Cu + HCl
Sulphonation H 2 S 2 0 7
(2) R-X R e d P - H i , L i A l H4 (3) -> Alkyl Sulphonic acid
+ H O H or RO H
(3) R-Mg-X orNH 3 orRNH2

S 0 + G 1 Reed reaction—^ R S Q Q
2 2
hv
Na , dry ethe r
(4) RX Wurtz reaction
A1CL /HC1 • , , „
Zn > branched alkanes
Isomerisation
(5) RX Frankland's reaction|
R - C - C l or R OH Pyrolysis
RedP/Hi SOO-TOO^-Alkenes+ CH4 o r C2H6
(6)
0
or Cr or Mo or V oxide
(7) + A1 2 0 3 500°C
' Aromatic compound
or RCHO
R- C- R
O
(8) Higher alkane

step up reaction
R- C- R Zn- H g / Cone . H Cl
(7) Clemension's reduction
0
CO. + H„0
R-C = O H 2 N- NH 2
Combustion
(8) 1
Wolf / Kishner reductiori
R
or
(RCH2CH2)3B
N a OH + C a O
( 9) RCOONa
(10) Kolbe's electrolyte synthesis
RCOONa
feBansal Classes HYDROCARBON [2]
REACTION CHART FOR ALKENES

( GMP )
C GR
J
conc.H 2 S0 4 H, Ni
(1) R- CH-CH- OH (1) 200-300°C
> R-CH-CH3
-H.,0
(2) R- C H - C H - X
ale. KOH (2) ^R-CHX-CH 2 X
-HX (3) HX R-CHX-CH3

R-CH=CH, >
Zn dust
or (4) HBr, Peroxide ) R- C H - C H Br
(3) R- CH - CH <* for higher alkene
-X, C H,
n 2n
(5) HOCl ) R - C H ( O H ) - C H CI
R - C H - C H . Zndust dil.H 7 S0 4
>
(4) (6) + H 0 R-CH2(0H)-CH3
X X I/ 2 Q 2 .R-C H-C H?
(7) Ag300°C
Ni,H, O
S
(5) R-C CH
200-300°C R-CH-CH9
( 8) +ch
2N2
(6 ) ^ ^ COOK Kolbe's electrolytic synthesis CHO
RCH-COOK
(9) _J 5^ (R CH 2 CH 2 ) 3 B
RD
+
CO + H 2
CO+H-, ) -C H-C H3 R - C H .2- C H 2
(7) (C 2 H 5 ) 4 N O H
(10) HCO(CO)4
>
'CHO
+
Pyrolysis CHO
^ R-C-O-CH2-CH2-R o.
O
(11) >CO2 + H2O
A
(9) R-H Pyrolysis R - C H - C H ,

(12) 0 CS ov 4
CuR. OH OH
(10) C H = CH C1
Bayer reagent R - CH - CH,

z
= 7 , i
(13) 1 % alkalineKMnO.
OH OH
R
(14) strong oxidant ) C OH + + jj q
Per acid R-CH-CH2

(15)
Pr iles -chalev's reaction o
o,+H,0
(16)
Ozonolysis C^ H
O O
(17)
200°ChighP
Polyalkene
Cl 2
>
(18) Substitution product
500°C
A1 2 (SQ 4 ) 3
(1 9 ) Isomerisation
200-300°C
(20) acetic anhydride R- CH =C H- CO CH

; t 2 3
Methyl alkenyl ketone

ALKANE
(21) > Higher alkane
faBansal Classes HYDROCARBON [3]
REACTION CHART FOR ALKYNES

( gmp
C gr
3
1) CH2Br-CH2Br ale. KOH or NaNH ,
(1) C H C H
^ 2 4 ' 2 6
Ni
2) CH3-CHBr2 alc.KOH,NaNH 2
(2)
Ag powder HBr
3) CHC13 A (3) —>CH,BrCH,Br
C2H2 Peroxide
J
'
Zn dust
4) CHBr-CHBr; (4) HBr
[NoPeroxide C H 3 - C H B r ,
(5) Hoci y, CI CHCHO

CHBr
5) Zn
(6) HCN jB a(CN) 2 ) CH,=CHCN
CHBr T
(7) CH3COOH,Hg' ^CH3CH(OCOCH3)2
6) CH=CH-C1 alc.KOH,NaNH0
(8) -> CHCHO

H C - C O Q N a Kolbe's electrolytic synthesis (Kucherov's reaction)
N
7) (9) Cone.H,SO, .CH,CH(HSO,)2
HC-COONa
AsCl,
H,0
8) CaC2 (10) Ca det& Bunsen reaction CHClCHAsCL
electric arc, 1200°C
9) 2C + H2 >
Berthelot'sprocess
(11) HgS0 4
CH?CHO
10) CH3-CSCH (i)Na (ii)R-X
CO+HOH
(i)CH3Mg!(ii)R-X (12) ' CH =CH-COOH
10) CH-CsCH Ni(CO)4
CO + EtOH
(13) Ni,160°C
* CH=CH-COOEt
(14) NaNH, .Na-CsC-Na
AgNO, +N114OH
(15) „ „ , , * Ag-CsC-Ag
(Tollen s nRe agent) °
b
(16) C U 2CI 2+ NH 4 OH ) Cu-C=C-Cu

(17) Combustion O2 _»C0 + H,0
2
CHO
(18) Bayer Re agent
•-> HCOOH
CHO
(19) > H-C-C-H +H2Q HCOOH

Ozonolysis I ' ~
o o
Trimerisation
(20) (Re d hot iron tube) benzene
Trimerisation
(21) »CgH8or 1,3,5,7-cyclo octa tetraene
[Ni(CN)2 ]
Dimerisation
(22) +
"^butenyne
[Cu(NH 3 ) 2 ]
CH-CH
(23) —» II II
CH-CH
S
CH,OH CH(OCH3)2
3 )
(24) (BF 3 -HgO) CH-,
methylal
^Bansal Classes HYDROCARBON [41
EXERCISE-I (A)
Q. 1 The reaction ofE-2-butene with CH212 and Zn-Cu Couple in either medium leads to formation of
CH CH, CH, CH,
H> H
(B) H/\ /\ CH 3 c n , y y ci -i ? CH3/
(A) ( C) ( D )
Q. 2 The product formed upon heating camphene with HCl is
(A) (C)
CI
Q3 (E)-3 -bromo-3 -hexene when treated with CH 3 O e in CH,OH gives

(A) 3-hexyne (B) 2-hexyne (C) 2.3-hexadiene (D) 2,4-hexadiene
Q. 4 The reaction of cyclooctyne with HgS0 4 in the presence of aq. H 2 S0 4 gives
(a ) (b> (c (d)
GC CC O
Q. 5 Order of reactivity of the following diene x, y and z in Diels-Alder reaction is
(x)L ? (y)l ( z)
(A) x > z > y (B) y >x > z (C) y > z > x (D) x > y > z
Me
11 DU u gQ
2
Q. 6 The major product P formed in g i v e n ] ,, —±-> P reaction is
HO-f-H
Me
p h C H 3 p h H
V _ / w
(C) '/'C (D) reaction will not take place
V
H H,C
fa Ban sal Classes HYDROCARBON [5]
Q 7 +Br2 mixture of product. Among the following which product will formed minimum
amount.
Br
(A) Br (B) \ ft (C)
H 2 H
Q.8 ^ ° - M ^ P ( M a j o r ) - ^ Q ( Major)
The structure of Q is
Br
Br
Br Br
(A) (B) (C) (D)
CH 3 M IS
[f (i)CH,COOOH ^
Q9 x
hACH3-^^
The probable structure of'X' is
CH 3 CH, CH,
CH,
-OH -OH -OH
18 H" 18 .
"OH (C) -OH
(A) (B)HO- -H -OH
-OH
CH, CH, CH,
CH,
Ph- -CH 3 Br, . Nal

1 0 * P(Alkene) Q (Alkene)
Q H,C- -Ph A" CC1, Acetone
OCOR
Alkene (P) & (Q) respectively are
c h
Phx /CH3 CH3\ / 3
Phx //CH3
(A) Both h H,C Ph Ph Ph

Ph
CH, CH 3
yPh
l3 \ /
(C) Bo th Ph-CH C^ (D) Both Ph / \ Ph
Me CH2
Q.ll Ozonolysis of CH3-CH=C=CH2 will give

(A) Only CHjCHO (B) Only HCHO
(D) Mixture of CH3CHO, HCHO & C 0 2
(C) Only C0 2
HYDROCARBON [6]
faBan sal Classes
Q. 12 O-xylene on ozonolysis will give

O CH3-C = O o
CHO
(A) | & CH3-C-CHO (B) C H 3 _I = 0 & CH 3 -O -C HO
CHO
CH3-C = O o
CH. - C = O CH O CHO
(Q & ( D ) C H 0 _ C H 0 &
CH3-C = O CHO CH3-C = 0 ' 3 " CHO
COOCH,
0 S 0 4 (leg)
Q.13 •» X.
-COOCH3 H 2 0/ Acetone
Identify'X'.
,COOCH 3 COOCH,
OH OH
(A) OH (B) OH
COOCH, COOCH,
COOCH3
HO OH
(C) (D) Reaction will not occu r
HO OH
COOCH,
OC 2H5 PdCL.HOH
Q.14 ^z.
CuCi,,0,
OC 2 H 5 OC 2 H5
OC 2 H 5
0 0
CH, CH,
I I ' 0s04(lequiv.)
Q.15 CH, - C = C - CH 0 - CH = CH, A; Identify A
(Acetone/water)
CH3CH3 OH OH CH 3 CH 3
(A) CH 3 - C = C - CH , - CH - CH 2 (B) CH 3 - C — C - CH 2 - CH = CH,

I I
OH OH
CH, CH,
I I
(C) C H 3 - C H — C C H 2 - C H - C H3 (D) Reactio n will not occur
I I
OH OH
[215]
l & B a n s a l Classes HYDROCARBON
Q, 16 | J + CH 2 N 2 (1 equi.) Pb
(QAc)2 ) B ; identify B
(A)S[ (B) I (C)L/J (D)
Q.17 1 -Penten-4-yne reacts with bromine at - 80°C to produce:

(A)4,4,5,5-Tetrabromopentene (B) ].2-Dibromo-l 4-pentadiene
(C) 1,1,2,2,4,5-hexabromopentane (D)4,5-dibromopentyne
Q. 18 Compound (A) on oxidation with hot KMnO^/ OH® givestwo compound

O
II
CH 3 - CH - COOH & CH3 - C - CH 2 CH 2 CH 3
CH3
compound A will have structure.

(A) CH 3CH 2 - C = C - CH 2 CH 3 (B) CH 3 - CH - CH = C - CH 2 CH 2 CH 3
CH 3 CH3 CH3 CH 3
(C) CH3CH - C s C - CH3 (D) CH 3 - CH - C = C - CH - CH 3
CH3 CH 3 CH3
Q.19 Consider the following reaction
(A)C 6 H 12 k m ^ / o h / a >C H O
s 10
In the above reaction (A) will be
(A) CH 3 -CH 2 -CH 2 -CH 2 -CH=CH 2 (B) CH3 - CH - CH 2 - CH = CH 2
CH 3
(C) CH3 - CH 2 - CH - CH = CH 2 (D) CH 3 CH 2 CH 2 - C = CH 2
CH3 CH3
Br
Q.20 f ^ J f ^ alcoholic KOH ) product
Major product is:
( c ) ( d )
o c t ( b ) o f 0 - 0 -
Q.21 Number of required 0 2 mole for complete combustion of one mole of prop ane -
(A) 7 (B) 5 (C) 16 (D) 10
faBa nsal Classes NOMENCLATURE OFORGANIC COMPOUND

[8]
Q. 22 How much volume of air will be needed for complete combustion of 10 lit. of ethane -
(A) 135 lit. (B) 35 lit. (C) 175 lit. (D) 205 lit.
Q.23 When n-butane is heated in the presence of A!Ci3/HCl it will be converted into -
(A) Ethane (B) Propane (C) Butene (D) Isobutane
Q.24 The reacting species of ale. KOH is -

(A) OH (B) OR' (C) OK" (D) RO
Q.25 The product of reaction between one mole of acetylene and two mole ofHCHO in the presence of
Cu2Cl2 -
(A) HOCH, - C = C - CH2OH (B) H2C = CH - CsC - CH2OH
(C) HC = C - CH2OH (D) None ofthese
Q.26 PMA polymer is formed by methyl acrylate, which is prepared as follows -

C +CH3 H
(A) R - C = CH _co±B°!L_> ( B ) HC 3 CH - ° ° >
' Ni(CO)4
(C) HC = CH (D) None ofthese

Ni (CO ) 4
Q.27 During the preparation of ethane by Kolbe's electrolytic method using inert electrodes the pH of the
electrolyte -
(A) Increases progressively as the reaction proceeds
(B) Decreases progressively as the reaction proceeds
(C) Remains constant throughout the reaction
(D) May decrease of the the concentration of the electrolyte is not very high
Q.28 Ethylene forms ethylene chlorohvdrin by the action of -

(A) Dry HCl gas (B) Diy chlorine gas
(C) Solution of chlorine gas in water (D) Dilute hydrochloric acid
Q.29 Anti-Markownikoff's addition ofHBr is not observed in -

(A) Propene (B)But-2-ene (C) Butene (D) Pent-2-ene
Q.30 Which alkene on heating with alkaline KMn0 4 solution gives acetone and a gas, which turns lime water
milky-
(A) 2-Methyl-2-butene (B) Isobutylene
(C) 1-Butene (D) 2-Butene
Q.31 Acetylene may be prepared using Kolbe's electrolytic method employing -

(A) Pot. acetate (B) Pot. succinate (C) Pot. fiimarate (D) None of these
Q.32 B < Imflar R-QC-R Na/NH3 > A
A and B are geometrical isomers (R-CH=CH-R) -

(A) A is trans, B is cis (B)Aand B both are cis
(C) A and B both are trans (D) A is cis, B is trans
Q . 3 3 Which is expected to react most readily with bromine -
(A) CH3CH2CH3 (B) CH 2-CH 2 (C) CH=CH (D) CH 3-CH=CH 2
Q. 34 By the addition of CO and 11,0 on ethene, the following is obtained -

(A) Propanoic acid (B) Propanal (C) 2-Propenoic acid (D) None of the above
Q.35 An alkyne C 7 H 12 on reaction with alk. KMn0 4 and subsequent acidification with HCl yields a mixture
CH3-CHCOOH
of i + CH ,C H 2 C00H The alkyne is -
(A) 3-Hexyne (B) 2~Methyl-3-hexyne

(C) 2-Methyl-2-he xyne (D) 2-Methyl- 2-hexen e
Q. 3 6 A compound (C5Hg) reacts with ammonical Ag N0 3 to give a white precipitate and reacts with excess of
KMn0 4 solution to give (CH 3 ) 2 CH-COOH. The compound is -
(A) CH 2 =€H-CH=CH-CH3 ' (B)(CH 3 ) 2 CH-CsCH
(C) CH 3 (CH 2 ) 2 C=CH (D) (CH 3 ) 2 C=C=CH 2
Q. 3 7 Which ofthe following reagents cannot be used to locate the position of triple bona in CH 3 -C=C"CH 3
(A) Br2 (B)03 (C) Cu 2 + (D) KMn0 4
A
3
Q.38 CH 3 -C H 2 -C= CH c ^ CH 3 C=C-CH 3
A and B are -
(A) alcoholic KOH and NaNH 2 (B) Na NH, and alcoholic KOH
(C) NaNH 2 and Lindlar
BH, / THF trn+ (D) Lindlar and NaN H2
A and B are -
(A)Both<^)-CH 2OH (B) Bot h^) x-CH3
( C) O C Hj OH, Q - C H , (D) Q - C H , Q-C H 3 OH
BH3
Q.4 0 B < ™F CH3-CS;CH HgSo 4 /H 2 so 4 A
H2O2 OH"
A and Bare-
O O
II II
(A) CH C H C H O , C H - C - C H (B) C H - C - C H C H C H CHO
3 2 3 3 3 3 3 2
(C) CH 3 CH 2 CHO (both) (D) CH 3 - C - CH 3 (both)
NaBD,
0 41 CH 3CH=CH 2 product X
Xis-
(A) CH3 - CH - CH 2 D (B) CH3 - CH - CH 2 0 H
OH D
(C) CH3 - CH - CH3 (D) none is correct
OD
cc
Q. 42 CH 2 =CH-CH=CH 2 V i r > product. The major product is -
(A) Br- CH2 -CH=CH-CH2 -CCl 3 (B) CH 2 = CH - CH - CH 2 - CC13
Br
(C) CH2 = CH - CH - CH 2 - Br (D) None is correct

!
CC13
Q.43 Mixture of one mole each of ethene and propyne on reaction with Na will form H2 gas at S.T.P. -
(A) 22.4 L (B) 11.2 L (C )3 3. 6L (D) 44.8 L
Q.44 Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol gave two alkenes Aand B. The ozonolysis products
ofA and Ba r e -
O
II
(A) A gives (CH3 ) 3 C-C - C(CH3 ) 3 and HCHO
B gives CH 3 - C - CH 2 - C(CH3 ) 3 and HCHO
(B) A gives (CH3 ) 3 C - C - C(CH3 ) 3 and HCHO
O CH 3
B gives CH, - C - C - C(CH 3 ) 3 and HCHO
1
CH 3
(C) A gives ( C H 3 ) 3 C-C- CH(CH3 )2 and HCHO
Bgives (CH 3 ) - C H . - C - C ( C H 3 ) 3 and CH3CH 2CHO

(D) None of these
NH4C1
>
Q.45 CH^CH , product
Product is -
(A) Cu-C= C-Cu (B) CH 2 =CH- C^CH (C) CH=C-Cu (D) Cu- C^C -N H 4
CH 3 CH 3
Q. 46 CH 3 - C = GH - C - CH 3 Naio4/KMnQ4 ^ products, Products are -
CH 3
O O
il II
(A) CH 3 - C - C H , , ( C H 3 ) 3 C-COOH (B) C H 3 - C - C H 3 , (CH 3 ) 3 C-CHO
(C) CH 3 - C - OH , (CH 3 ) 3 C-C OOH (D) None is correct
O
/ H
Q.47 Alkene A °3 2° ) C H 3 - C - C H 3 + CH 3 COOH + CH, - C - COOH
O
A can be -
C(CH 3 ) 2
CHCH,
,CH 3 I!
(A) CH 3 -C-CH=C:
^CH, (B) CH 3 - C - CH = HC - CH 3
(C) Both correct (D) None is correct
Q.48 reagentR, reagent R,
HO OH HO OH
Rj and Rj are -
(A) Cold alkaline KMn0 4 , 0s0 4 / H 2 0 2 (B) Cold alkaline KM n0 4 , HC0 3 H
(C) Cold alkaline KM n 0 4 , C H 3 - 0 - 0 - C H 3 (D) C 6 H 5 C0 3 H, HCO ,H
CH .
H-C
Q.49 II alkalineKMnQ4 ^ ^ which. is tme about this reaction?
H—C
CH 3
(A) A is meso 1 ,2- but an- di- ol formed by syn addition

(B) A is meso 1, 2-bu tan -di -ol formed by anti addition
(C) A is a racemic mixture of d and /, 1,2-buta n-d i-ol formed by anti addition
(D) A is a racemic mixture of d and 11,2-bu tan -di-ol formed by syn addition
l&Bansal Classes HYDROCARBON [12]
Q. 50 ( /—O + C H : M g B r H30 + Â Con.H2S04 > R Q 3 /H 2 0/Zn )

r.
A, B and C are -
A B C
3 3
HO CH, F F
(A) °"HO
HO CH 3 CH, O
(B) IHCHO
HO CHj CH, CH,
(C) I I r i r g»
HQ. jCH, CH, CH,
(D) OOH
Q S 1
V J ^ '
A can be-
(A) Cone. H 2 S0 4 (B) alcoholic KOH (C )Et3 N (D)t -BuOK
Q. 52 BrCH2 -C H 2 -C H 2 Br reacts with Na in the presence of ether at 100 °C to produce -

C H 2 - CH2
(A) BrCH2 -CH=CH 2 (B) CH2=C=CH2 (C) \ / (D) All of these
Q. 53 Which has least heat of hydrogenation -
( A ) / = \ ( B ) y = y (C ( D ) ^ > =
CH,3
\ (l)Hg(0Ac)2/H20/THF ?
V 3 (2)NaBH4 NaOH Ii 20 A.AlS-
OH
CH, / rr-OH 4-CH, , rr-CH,
( A) / 3—OH
n_r»o (B )C
(E) I 3\ (C) (D)
Q. 55 An organic compound ofmolecular formula C4H6, (A), forms precipitates with ammoniacal silver nitrate
and ammoniacal cuprous chloride.' A' has an isomer 'B', one mol of which reacts with one mol ofBr2 to
form 1,4-dibromo-2-butene. Another isomer of A is 'C \ one mole of C reacts with only 1 mol. of Br,
to give vicinal dibromide. A, B & C are
(A) CH 3 - C H 2 -OCH and CH 2=CH-CH=CH 2 ; f j |
(B) CH 3 -C=C-CH3 and CH 3-CH=C=CH2 ; CH 3 -C=C-CH3
CH9\ C H 2 -CH
(C ) I ~ . O C H , and ; CH 2 = CH-CH=CH 2
CH ,/ C H 2 -CH
-CH.
(D) CH 3 - C S C - C H 3 and CH 2 | CH2 ; CH 2 = CH - CH = CH 2
^ C H ^
Q.56 CH 3 -CH=CH-CH3 product is Y (non-resolvable) then X can be -

cis
(A) Br2 water ( B) H C0 3 H
(C) Cold alkaline KMn0 4 (D) all of the above
Q. 5 7 Electrophilic addition reaction is not shown by
(A) CH 2 = C - CH 3 and Br 2 (B) CH=CH2 and HO-C1
CH 3
(C) CH 3 -CsCH and CH3MgBr (D) CH2=CH2and dil. H2 S0 4 solution
Q. 5 8 A mixture of CH4, C 2 H4 and C2 H 4 gaseous are passed through a Wolf bottle containing ammonical
cuprous chloride. The gas coming out is
(A) Methane (B) Acetylene

(C) Mixture of methane and ethylene (D) original mixture
Q. 5 9 In the presence of strong bases, triple bonds will migrate within carbon skeletons by the
(A) removal of protons (B) addition of protons
(C) removal and readdition of protons (D) addition and removal of protons.
CHCOOH
Q.60 CH 2 =CH-CH=CH2 + -> product X by reaction R X and R are
CHCOOH
COOH COOH
« a
a
Diels Alder COOH Friedel-Crafts
COOH
COOH
y^yCOOR
( Q l O i . Diels Alder (D) Friedel-Crafts
COOH COOH
Q. 61 For the ionic reaction of hydrochloric acid with the following alkenes, predict the correct sequence of
reactivity as measured by reaction rates:
(I)C1CH=CH2 (1I)(CH3)2.C=CH2 (i n) OHC GH=CH2 ^V)<NC) 2C=C(CN)2
(A) IV > I > III > II (B) I > IV > II > III (C)I I I > I I >I V > I (D) II > I > III > IV
Q. 62 The addition of bromine to 2-cyclohexenyl benzoate in 1,2-dichloroethane produces dibromo

derivatives:
(A) 2 (B)3 (C)4 (D)6
Q. 63 How many products will be formed when methylenecyclohexane reacts with NB S?

(A) 3 (B )l (C)2 (D)4
CH3-C-NH2
Br
Q.64 />~ - Mg/drycther^pQ O ^(Y)
The structures of (X) and (Y) respectively are
(A) X = < V-MgB r ; Y=< V o H
(C)X= < ^ ^ M g B r ; Y=
(D) X - BrMg ^ MgBr ; Y = HO- OH
faBansal Classes HYDROCARBON 115]
EXERCISE-I (B)
A HgS04/H2SQ4 ^
Q.l B
BH,/THF
H 2 O 2 /OH
B is identical whe n A is -
(A) H - h - H (B) — H (D)
(Q
Q.2 An alkene on ozonolysis yields only ethanal. There is an isomer of this which on ozonoly sis yields:
(A) propanone (B) ethanal
(C)methanal - (D) only propanal
Q.3 CH 3 - CH = CH-CH, + CH 2 N 2 — ~ > A

A can be
(A) A (C)
Q.4 Aqueous solution of potassium acetate is electrolysed. Possible organic product s are:
(A) n-Butane (B) C 2 H 5 COOC,H 5 (C) CH 3 -CH 3 (D) CH 2 =CH 2
Q.5 Re agent R2 Reagent R,
HO HO OH
R, and R 2 are:
(A) cold alkaline KMn0 4 , 0 s 0 4 / H 2 0 2 (B) 0 s 0 4 / N a H S 0 3 ; Ag0 2 , H 3 0®
(C) cold alkaline KMn0 4 , C 6 H 5 C 0 3 H / H 3 0® (D) C 6 H 5 C 0 3 H ; 0 s 0 4 / NaHS0 3
H2/Pt
Q.6 (A) C 4 H 6 > (B) C 4 H g -> CH 3 COOH
Hence A and B are
(A) CH 3 C = CCH 3 , CH 3 CH = CHCH 3 (B) CH 2 = CHCH 3 = CH 2 , CH 3 CH = CHCH 3
(C) CH 3 CH = CHCH 3 (D) None
Q. 7 Which is / are true statements/ reactions?

(A)A14C3 + H 2 0 — > C H 4 (B) CaC 2 + H 2 0 > C 2H2
(C) Mg 2 C 3 + H 2 0 > CH 3 C =CH (D) Me 3 C - H + a q . K O H — ^ M e 3 C - O H
Q.8 P H- C - CH, Ph-CH 2 -CH 3
A could be:
(A) NH 2 NH 2 , glycol/OH (B) Sn(Hg)/conc. HCl
(C) P/HI (D) CH 2 - CH 2 ; Raney Ni -H^
SH SH
BuOK
Q.9 — >Product
which is / are correct statements about the product:
(A) -CH, is an endocyclic Saytzeff product
CH,
(B)
a is an exocyclic Saytzeff product
(C) CH, is an exocyclic Hoffmann product
(D) C H is an endocyclic Hoffmann product

C V 3
NBS
Q.10 CH, = CHCHXH = CH2 > A, A can be
(A) CH, = CH CH CH = CH, (B) CH2=CHCH=CH-CH2Br
Br
(C) CH2 = CH CH2 CH = CHBr (D) CH 2 = CH CH 2 C = CH 2
Br
Q.ll Which are correct statements?
(A) meso-1, 2-dibromo-butane on reaction with Nal / acetone gives trans-2-butene
(B) d-or /-1,2-dibromobutane on reaction with Nal/acetone gives cis-2-butene
(C) meso -1,2-dibromo-butane on reaction with Nal / acetone gives cis-2-butene
(D) d-or/-1,2-dibromobutane on reaction with Nal/acetone gives trans-2-butene
Q.12 Ph-CH-CH2 + BrCCl, Pôxide )
Product is:
H H
(A) Ph- -CH2CC13 (B) Ph- - CH?Br
Br CCI3
Br CCI3
(C) Ph- •CH2CC13 (D) Ph- •CH2Br
Q.21 In most of the rearrangements, the migrating group migrates with

(A) inversion of its configuration (B) retention of its configuration
(C) racemization ofits configuration (D) retention of its structure
Q.22 Indicate among the following the reaction not correctly formulated.
(A) CH2=CH-CH3 > O^Cl-CHCl-CHG
H C ^ X
(B) HCsC H+CH^ > II N
HC y
1-1
photo
(C) (CH3)3CH + Cl2 ~ > (CH3)3C-C1 as major product
haiogenation
(D) CHJ-C^C-CHJ-C^-CHJ J><CH2_ C H 2 _ C H 3
Q.23 List I List II

(A) n-Hexane Cr203-Ai203,A ^ (1) Substitution reaction
(B) CH s CH RedhotFetube > (2) Elimination reaction
CH3
( C ) C H 3 -C- X > aq. (3)Aromatisation

I
CH3
(D) CH3-CH2-X > ale. KOH (4) Cyclization
Q.24 Li st I List n
(I)B
(A) CHL3 - C = CH,2 % ) (1) CH 3 -CH2-CH=CH2
| (ii)H 2 0 2 /0H
CH 3
(B) CH 3 - C = CH 2 ^QA°VHOH) (2) CH 3 -CH=CH-CH 3

(ii)NaBH4
CHQ
CI
(C) CH 3 - CH 2 - CH - CH 3 CHJONA/A ) (3) CH 3 - C H - C H 2 O H
CH.
CI OH
(CH
(D) CH 3 - C H 9 - C H - C H , 3)3CONA ) (4) C H 3 - C - C H 3
I
CH.
Codes : A B C D
(a) 4 3 1 2
(b) 4 3 2 1
(c) 3 4 2 1
(d) 3 4 1 2
Q.25 Lis t I Listn

(A) Walden Inversion (1) Cis addition
(B) Racemic mixture (2) Trans addition
Baeyer
(C) Alkene > (3) SN, reaction
(D) Alkene (4) SN2 reaction

Codes: A B C D
(a) 3 4 2 1
(b) 3 4 1 2
(c) 4 3. 1 2
(d) 4 3 2 1
Q.26 (A) CH 3 -C=C-List

CH 3I — c i s - 2 - b u t a n e (1)Na/NH 3 (/) List n
(B) C H 3 - C = C - C H 3 >trans-2-butane (2)H 2 /Pd/BaS0 4
(C) CH 3 C=C-CH 3 > 1-Buty ne (3) ale. KOH, A
(D) CH 3 - C H 3 - C = C H — 2 - B u t y n e (4) NaNHj , A
Codes: A B C D
(a) 2 1 3 4
(b) 1 2 4 3
(c) 1 2 3 4
(d) 2 1 4 3
Q.27 List I List n

electrolysls
(A) RCOONa > R-R (1) Corey-Housh reaction
Soda lim e , „ „
(B) R-CH2-COOH —>R-CH 3 (2) Kolbe electrolysis
(i)Ag NO,
(C)RCOOH •R-Cl (3) Oakwood degradration
(ii)CI2/A
(D) R'-X + R^CuLi > R-R' (4) Hunsdiecker reaction

Codes: A B C D
(a) 2 3 4 1
(b) 1 3 4 2
(c) 2 4 3 2
(d) 2 4 1 3
Q.28 ListI Listn
0
CH2-CH3
C —CH,
(A) (1) Birch reduction
o
II CH2-CH3
C —CH,
(B) (2) Stephen's reduction
HO
(C) (3) Wolf-Kishner reduction
(D) (4) Clemmensen reduction
Q. 29 List I List n
(A) n-Hexane » Benzene (1) Wurtz reaction
(B) CH=CH » Benzene (2) Coupling of reactants is taking place
(OCH^CH^CHj > 2,2,3,3 tetramethyl butane(3) A1CL + HCl at 3 00°C
(D) CH3-CH2-X > n-Butane (4) Polymerisation
(5) Aromatic procducts is formed
(6) Zn + A used as reagent
(7)Al203 at high temperature
Q.30 List I List n

Baeyer
(A) Alkene >? (1) Neighbouring group participation seen
(B)Alkene-^>? (2) Markovnikov's rule is followed.
H 2 Pd. .
(Q =~ — >9 (3) Cis isomer formed
BaSO.
PhC 3H
(D) Alkene ° >? (4) Syn addition
followed
by H30®
(E) C H , - C = C H 2 (i)Hg(OAc)2/HOH ) (5) Anti addition

| (ii)NaBH4
CH,
(6) Racemic mixture in case of But-2-ene (cis)
(7) Meso compound in case of But-2-ene (cis)
EXER CISE-II
Q. l Give the product of
R ^ V ^ I 3.THF
1.BD3
(a) f
W
T (b)COOH.> < . H D >
\ > V / THF H COOH 2.D 2 0 2 ,D0
CH 3
LlA 1H ?
Q-2 CH 3- C- C1 * >
i
CH 3
Q. 3 What are the ozonolysis products of
C
2H5\ /C2H5 , RF RN IT
Q.4 / c = c
\ — 3 3
> A + B.W h a t a r e A a n d B?
H H 2. H,OZH+
Na H
Q.5 k M ° > A. Write the structure ofA.
ALC
D Y H -
Br
O O
II II
CH. .CH
Q. 6 ^c=c ^ 22 ,, A. Write the structure of A
NO 2 -C H 2 CH 2 -N O 2
CH
Q.7 j' — A . Write the structure ofmaj or product A.
Q.8 Give the structure of the alkene that yields on ozonolysis

(i) CH3CH2CH2 CHO & HCHO (ii) C 2 H 5 COCH 3 & CH 3 CH(CH 3 ) CHO
(iii) Only CH3 CO.CH3 (iv) CH 3 CHO & HCHO & OHC CH2 .CHO
(v) Only OHC- CHj C^C H^- CHO .
Q. 9 One of the constituent of turpentine is a-pinene having molecular formula C 10 H, 6 . The following scheme
give reaction of a-pinene. Determine the structure of a-pinene & of the reaction products Athrough E.
E(C 10 H 18 O 2 ) A(C 10 H 16 Br 2 )
T tÔ t.Br2 /CCl 4
C 10 H 16 O(D) < phC03H a -pinene o >B (C 10 H 1? OBr)
(i) H 2 S0 4
0s04 (i) 0 3
(ii) A
H2 (ii) Me2S
F r ' ° C(C t0H15 Br)
Q.10 Propose structures for intermediates & products Ato K
e t t o
bromobutane >D ' C H 3 ( C H ; ) 3 -CH (K
2, H,0+
KOII, ILO RSO/.A
Na
fused KOH
followed bv NaNH,
Q.ll Identify the following (A to D).
D + = O + CH,CO,H
optically active
KMn04(hot)
C h, r L i ndl a x '' s C,,H„ Li/EtNH

*. 4 ethyl 2, 4 dimethyl
g Catalyst ^ 2, 5 heptadiene
optically
active 0,/H,o
CSH.„04 + ™ e >C = 0 + CH 3CO,H

optically inactive
C.
Q.12 What are A to K for the following reactions

(i) PhC = CH + CH 3MgX -> A ^ a ) g u/nh, ) r
(ii) PhCHjCHjCHg + Br 2 >D -» E cold dil. KMnQ4 ^ p hot KMnQ4 ^ Q
vOH
CH,
(Mi) (iv)
Me Me H3C OH OH
OH
(v) CF3 - CH = CH2
Me Me
(!lBansal Classes HYDROCARBON [24]
->
(i) A A
\ COjMe
o
('")
+
J
H Ph
A I
o
l.NaNH2(3equiv.)NH3 ^ g
2. CH3I
Q 14 (i) Compare the reaction of CH2 = CH, & CF2 = CF2 with NaOEt in EtOH
(ii) CC1, = CC12 does not decolourise Br2 solution - explain.
Q.15 Account for the collowing facts

(i) Ozonolysis if carried out in MeOH solvent a hydroxy peroxy ether is formed as unexpected product.
(ii) When 2,3 dimethyl 2 butene is treated with 0 3 in presence ofHCHO in CH,C12 medium, an ozonide
other than that expected of the starting alkene is formed. Identify the unexpected ozonide.
Q.16 Explain the following:

(i) 1,2 shift does not take place during oxymericuration demercuration. Why?
(ii) Halogneation of alkene is anti addition but not syn addition. Why?
(iii) Anti markovnikov addition is not applicable for HCl. Why?
(iv) 1,4-addition hikes place in butadi-ene. Why?
(v) C-H bond is stronger than C-C bond but in chlorination C- H bonds get cleaved but not C-C bond.
Why?
Q.17 Conversion:
(i) C2H2 » racemic 2, 3 dibromobutane (ii) 2 butyne > 2 pentyne
(iii) Ethyne » Acetone (iv) Methane > n Butane (v) Ethene » Propionic Acid
Q.18 Conversion:
(i) C2H2 > ethylidene diacetate (ii) C ^ -—> Butyne diol
(iii) C,H, > m nitroaniline (iv) cis but 2 ene > Trans but 2 ene
Q.19 Outline a stereospecific synthesis of meso 3,4 dibromohexane from ethyne.
Q.20 How can you convert

(a) Ethane in to meso 2,3 dimethyl oxiran
(b) CaC, into 1,3. 5 hexatriene
(c) Trimethylsecbutyl amonium hydroxide into 1,4-butan-dial
(d) Cyclo hexanol into trans cyclo hexane-1,2-diol
Q.21 How will you conver

(a) Hexane dial into 1,3,5 hexatriene
(b) 1 -methyl propyl ethanoate into 1,4-dichloro-2-butene
fa Bansal Classes HYDROCARBON [25]
Q.22 Explain the mechanism of following conversion.
Me2C = CH - CH 2CH 2 CMe = CHCHO + H 3 0

Citral
Q.23 When citral is allowed to react in presence of dilute acid with olivetol, there is obtained a mixture of
products, one of which is drug marijuana. Reaction is as follows.
C H
Me2C = CH - CH 2-CH 2-CMe=CH-CHO + [ q ! H® ) / \ (0/~ ' "
O H ^ ^ Q H , — \ _ q )
(marijuana)
Explain the mechanism.
Q.24 The following cyclisation has been observed in the oxymercuration & demercuration of this unsaturated
alcohol. Propose a mechanism for this reaction.
2. NaBH 4
Q.25 Write the structural formula oflimonenefromthe following observation:

(a) Limonene when treated with excess I-^&Pt catalyst, the product formed is 1 isopropyl • 4 methyl cyclohexane
(b) When it is treated with 0 3 & then Zn/H 20 the products of the reaction are HCHO & following compound
Cu+
Q.26 (a) MeCH2-C=CBr + CH=CMe > A
CI
0H
(b) CH 2 -CHC1 2 >B
OH
(c) CH2 = C H - C H - C H = C H - C H , — l e O H > C
H2S04
(d) / \—C=CH
\ / H2SO4/H2O
(e) C13C-CH=CH2 HQBr > £

OH
rS
(0 / - Y * > F °3Z»"20 > G
Q.27 Acetylene is acidic but it does not react with NaOH or KOH. Why?
Q.28 CH=C-CH 2 -CH=CH2 , adds up HBr to give CH^ C-CH 2 -CHBr-CH 3 while CH=C-CH=CH2 adds
up HBr to give CH 2=C . Br . CH=CH2.
Q.29 Chlorination of ethane to ethyl chloride is more practicable than the chlorination of n-pentane to
1-chloropentane.
Q.30 Why 11-pentanehas higher boiling point than neopentane?
EXERCISE-HI
Q. 1 0.37 gm of ROH was added to CH3MgI and the gas evolved measured 112 cc at STP. What is the
molecular wt. ofROH ? On dehydration ROH gives an alkene which on ozonolysis gives acetone as
one of the products ROH on oxidation easily gives an acid containing the same number of carbon
atoms. Gives the structures ofR OH and the acid with proper reasoning.
Q.2 An alkane A (C5H, 2) on chlorination at 3 00° gives a mixture four different mono chlorinated derivatives
B, C, D and E. Two of these derivatives give the same stable alkene F on dehydrohalogenation, On
oxidation with hot alkaline KMn0 4 followed by acidification ofF gives two products G and H. Give
structures ofA to H with proper reasoning.
Q.3 There are six different alkene A, B, C, D, E and F. Each on addition of one mole ofhydrogen gives G
which has the lowest molecular wt hydrocarbon containing only one asymmetric carbon atom. None of
the above alkene give acetone as a product on ozonolysis. Give the structures of A to F. Identify the
alkenes that is likely to give a ketone containing more than five carbon atoms on treatment with a warm
conc, solution of alkaline KMn0 4 .
Q.4 3,3-dimethyl-1 -bu tene and HI react to give two products, C6 H, 3 I. On reaction with ale, KOH one
isomer, (1) gives back 3,3 -dimethyl-l-butene the other (J) gives an alkene that is reductively ozonized
to Me 2 C=0. Give the structures of (I) and (J) and explain the formation of the later.
Q. 5 Three isomeric alkenes A, B and C, C 5HR) are hydrogenated to yield 2-methvlbutane A and B gave the
same 3° ROH on oxymercuration - demercuration. B and C give different 1° ROH's on hydroboration
-oxidation. Supply the structures ofA, B & C.
Q.6 Two isomeric alkyl bromides A and B (C 5H, ,Br) yield the following results in the laboratory. A on
treatment with alcoholic KOH gives C and D (C 5H, 0 ). C on ozonolysis gives formaldehyde and
2 methyl propanal. B on treatment with alcoholic KOH gives only C (C 5 H]0 ). Deduce the structures of
A, B, C andD. Ignore the possibility of geometrical and optical isomerism.
Q.7 Give the structure of A, B and C.

(a) A. (C4Hg) which adds on HBr in the presence and in the absence of peroxide t o give the same product
C4H9Br.
(b) B (C4H8) which when treated with H 2 S0 4 / H 2 0 give (C4H10 O) which cannot be resoslved into optical
isomers.
(c) C (CgH12), an optically active hydrocarbon on catalytic hydrogenation gives an optically inactive
compound Cfi H, 4 .
Q.8 An alkylhalide, X, of formula C 6 H )3 Clon treatment with potassium tertiary butoxide gives two isomeric
alkenes Y and Z (C6H,2). Both alkenes on hydrogenation gives 2,3-dimethylbutane predict the stmctures
ofX, YandZ.
Q.9 Identify a chiral compound C, C, 0 H. 4 , that is oxidized with hot KMn0 4 to Ph COOH, and an achiral
compound D, C lt ,H ]4 , inert to oxidation under the same conditions.
Q.10 C7H14 (A) decolorises Br2 in CC14 and reacts with Hg(OAC)2 in THF. H 2 0 followed by
compound (C) obtained by oxidation of 3-hexanol with KMn0 4 . Identity A, B and C compound D,
and isomers of A reacts with BH V THF and then F I ^ / O H to give chiral E. Oxidation of E with
KMn0 4 or acid dichromate affords a chiral carboxylic acid F. Reductive Ozonolysis of D, gives the
4
F and G. '
Q.ll
Q.13 A can
B hydrocarbon A, ofthefrom
also be obtained formula
the C
gH10, on ozonolysis gives compound B (C 4 H6 02 ) only. The compound
alkylbromide (C3H5Br) upon treatment with magnesium in dry ether,
Q.14 An organic compound (A), C6H10 on reduction first gives (B), C 6H12 and finally (C), C H[4 . (A)
S S V 6 S m C2l
h "d fi d K M n O ^ ^ ^ ' ^ J4° ^ f E ) C
f f 2 0xi dat i
°no^B)
OF)'
Q.15 Compound A (C 6H]2 ) is treated withBr2 to form compound B (C6H12Br2). On treating B with alcoi
KOH followed by NaNH, the compound C (C6H10) is formed. C on treatment with H 2/Pt fo
2-methylpentane. The compound ' C does not react with ammonical Cu2Cl2 or AgN0 3 . When
treated with cold KMn04 solution, a diol D is formed which gives two acids Ea ndF when heatec
KMn04 solution. Compound E is found to be ethanoic acid. Deduce the structures fromAto F.
(A) givesnoj>pt. with Ag (N H 3 V andgfves optimally inactive (CX C 8 H, 4 ^ t h Hjnpre ser
Q.17 A
ozoJysis followed by hydrolysis gives two aldehydes D, C2 H 4 0 aid E, Oxidation ofB wi
HYDROCARBON [28]
Q.20 6g sample of a natural gas consisting of methane (CH4) and ethylene (C2H4) was burned with excess of
oxygen and 17.2g of carbon dioxide and some water was obtained as products. What percent by
weight of the sample was ethylene.
EXERCISE-IV (A)
Q. 1 Alcoholic solution ofKOH is a specific reagent for - [IIT4 90]
(A) Dehydration (B) Dehydrogenation
(C) Dehydro halogenation ' (D) Dehalogenation
Q.2 Of the following, unsaturated hydrocarbons are - [IIT'90]
(A) ethyne (B) cyclohexane (C) n-propane (D) ethene
Q. 3 1 -chlorobutane on reaction with alcoholic potash gives - [IIT 491]
(A) 1-butene (B) 1-butanol (C) 2-butene (D) 2-butanol
Q4 The hybridisation of carbon atoms in C-C single bond ofHCsC-CH=CH 2 is - [IIT '91]
(A) sp3-sp 3 (B)sp 2 -sp 3 (C) sp-sp 2 (D) sp 2-sp 2
Q.5 The product(s) obtained via oxymercuation (HgS0 4 + H 2 S0 4 ) of 1-butyne would be -
(A) CH3 - CH 2 - C - CH , (B) CH 3 -CH 2 -CH 2 -CHO

II
o
(C) CH,- CH 2 -CH0 + HCHO (D) CH 3 -CH 2-COOH + HCOOH
Q. 6 When cyclohexane is poured on water, itfloats,because - [I IT ' 97]

(A) Cyclohexane is in 'boat' form (B) Cyclohexane is in 'chair' form
(C) Cyclohexane is in 'crown' form (D) Cyclohexane is less dense than water
Q.7 Which ofthe following compounds will show geometrical isomerism? [IIT '98]
(A) 2-butene (B)Propene (C) 1-phenylpropene (D) 2-methyl-2-butene
Q.8 In the compound CH 2=CH-CH2-CH 2-C=CH, the C 2 -C 3 bond is ofth e type - [IIT 4 99]
(A) sp-sp2 (B) sp 3-sp 3 (C) sp-sp 3 (D) sp2—sp3
Q. 9 Which one ofthe following alkenes will react fastest with H2 under catalytic hydrogenation condition -
[IIT '2000]
R R R H R R R R
y- \ / \ / \ /
(A) ; > = ( (B) > = < (C) > = < CD) / \
H H R H R H R R
Q. 10 Propyne and propene can be distinguished by - [IIT42000]

(A) conc H 2 S0 4 (B) Br, in CC14 (C) dil. KMn0 4 (D)AgN0 3 in ammonia
Q. 11 In the presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti-Markovnikov
addition to alkene because - [T1TS42001]
(A) both are highly ionic
(B) one is oxidising and the other is reducing
(C) one ofthe step is endothermic in both the cases
(D) All the steps are exothermic in both cases
(B) An optically inactive [IIT'2001]

(D) Adiastereomeric mi?
Q.13 The reaction of I HOC! I ia the addition of • [IIT'2001J

(A) H+ (B) CR in first ste
(C) OH (D)C1 and OH
Q.14
Q.15 : MO W
H 3 C - C H - C H - C H 3 +Br -»'X'+:
D U
(A) H3C - CH - CH - C H 2 (B) H 3 C - C H - C - C H 3
I> CH 3
J, u
(C) H 3 C - C - C H - C H 3 (D) H 3 C ~ C H - C H - C H 3
1, U
Q.16
(A) bromine, CC14 (B)H2J
(C) dilute H 2 S0 4 ,HgS0 4 (D) ammonical Cu2Cl2

Q 17 C 6 H 5 -C=C-CH3 —
( A ) N A @ (B)Y-<o) (C) C6H< - C = CHCH 3 (D) C 6 H 5 - CH = c - CH 3
' in on
HYDROCARBON [30/
OH H+ x
2 5
Q.18 " _H 0 (mixture) > compounds of molecular formula C4H8Br 2
Number of compounds in X will be: |1IT'20031

(A) 2 (B) 3 (C) 4 (D) 5
Q.19 2-hexvne can be converted into trans-2-hexene by the action of: [IIT' 2004]
(A) H 2 -Pd-BaS0 4 (B) Li in liq. NH3 (C)H 2 -P t0 2 (D) NaBH4
Q.20 When Phenyl Magnesium Bromide reacts with tert. butanol, which of the following is formed?
(A) Tert. butyl methyl ether (B) Benzene
(C) Tert. butyl benzene (D) Phenol [IIT '2005]
Q.21 1 -bromo-3 -chlorocyclobutane when treated with two equivalents ofN a, in the presence of ether which
ofthe following will be formed? [IIT' 200 5]
/Br /CI
(A) (B) ( C ) [ J (D)
Q. 22 Cyclohexene is best prepared from cyclohexanol by which of the following:

(A) conc. H 3 P0 4 (B) conc. HCl/ZnCl2 (C) conc. HCl (D) conc. HBr
[ET '2005]
Q.23 CH 3 - C H C H 2 + NOC1 - » P [IIT 2006]

Identify the adduct.
CH3-CH-CH, CH3-CH-CH2
(A) I ! (B)
W
I I
CI NO NO CI
NO
J
, C Hi33, —
- C H 2, ~~
- CH
(C) , (D)
NO CI
CI
CH,
Q.24 H.CÎ Ci 2'hv ) Nfisomeric products) r ,H i ; Cl fractional distillation ) M(isomeric products)

CH
What are N and M?
(A) 6, 6 (B) 6, 4 (C) 4, 4 (D) 3, 3 [IIT 2006]
i&Bansal Classes HYDROCARBON [31]
EXERCISE-IV (B)
CI
Q.l (CH3) 2 C - C H 2 C H 3 _^KOH_ _ > ? [IIT 1992!
^ „ ale. KOH
Q.2 C6H5CH2CHCH3 —— > ? HBr ^ [ I I T 19931
Br
Q. 3 an optically active hydrocarbon which on catalytic hydrogenation gives an optically inactive
C ( C 6 H j 2 ),
compound, C 6 H, . [IIT 1993]
Q. 4 Draw the stereochemical structure ofthe product in the following reactions. [IIT 1994]
Ho
R-C EE C-R
Lindlar catalyst
Q. 5 Write down the structures of the stereoisomers formed when cis-2-butene is reacted with bromine.
[IIT 1995]
Q.6 An organic compound E( C 5 Hg) on hydrogenation gives compound F(C5H12). Compound E on ozonolysis
gives formaldehyde and 2-ketopropanal. Deduce the structure of compound E. [IIT 1995]
Q. 7 Give the structures of the major organic products from 3-ethyl-2-pentene under each of the following
reaction conditions. [IIT 1996]
(a) HBr in the presence of peroxide (b) B^ /F Ô
(c) Hg(0Ac) 2 /H 2 0;NaBH 4
Q.8 An alkyl halide, (X) offormula C6H13C1 on treatment with potassium tertiary butoxide gives two isomeric
alkenes (Y) and (Z) (C 6 H ]2 ). Both alkenes on hydrogenation give 2,3-dimethylbutane. Predict the
structures of (X), (Y) and (Z) [ITT 1996]
Q.9 3,3-Dimethyl-butan-2-ol loses a molecule ofwater in the presence of concentrated sulphuric acid to
give tetramethylethylene as a major product. Suggest a suitable mechanism. [IIT 1996]
Q. 10 One mole ofthe compound A (molecular formula C8H12), incapable of showing stereoisomerism, reacts
with only one mole of H 2 on hydrogenation over Pd. A undergoes ozonolysis to give a symmetrical
diketone B (C 8 H 12 0 2 ). What are the structure ofA and B? [IIT 1997]
Q. 11 Compound (A) C6H 12 gives a positive test with bromine in carbon tetrachloride. Reaction of (A) with
alkaline KM n0 4 yields only (B) which is the potassium salt of an acid. Write structure formulae and
IUPAC name of (A) and (B). [UT 1997]
Q.12 The central carbon-carbon bond in 1,3-butadiene is shorter than that of n-butane. Why?
[IIT 1998]
Q.13 Write the intermediate steps for each ofthe following reaction [IIT 1998]
C 6 H 5 C H ( OH ) C EE C H ->c 6 h 5 ch= ch cho
Q 14 Write the intermediate steps for each of the following reaction. [IIT 1998]
Q.15 Discuss the hybridisation of carbon atoms in allene (C3H4) and show the 7i-orbital overlaps
[IIT 1999]
Q.16 Complete the following - [IIT 1999]
Q.17 Complete the following - [IIT 1999]
D D HO c h
3
\ /
H,C—C H
/=c\ D
3
A . > H 33C— C
/ \ / N
H3C CH,. CH 3 CH 3
Q.18 Explain briefly the formation on the products giving the structures ofthe intermediates. [IIT 1999]
C H
2 \
HCl „
(i) r , + I /CH~CH 2 - C l + etc.
H,C OH > H,C
But
CH 3 CH,
! 3
CH H
HCl
(ii)
H,C OH H,C C CI
Ho
Explain the non formation of cyclic product in (ii)
Q.19 Carry out the following transformation in not more than three steps. | HI' 1999]
CH,-CH2 -C=C-H -> CH3 - CH, - CH 2 - C - CH ,
Q.20 CH2=CH is more basic than HC=C [IIT 2000]
Q.21 What would be the maj or product in each of the following reactions? [IIT 2000]
CH,
CH3-C-CH,Br C 2 H 5 OH ) H,
CH,
' ' I A (ii) Lindlar'sCatalyst
CH,
Q.22 On reaction with 4N alcoholic KOH at 175 °C 1-pentyne is slowly converted into equilibrium mixture
of 1.3% 1-pentyne (A), 95.2% 2-pentyne (B) and 3.5% 1,2-pentadiene (C). Give the suitable
mechanism of formation ofA, B and C with all intermediates. [IIT 2001]
Q.23 Identify X, Y and Z in the following synthetic scheme and write their structures. Is the compound Z
optically active? Justify your answer. [IIT 2002]
(i) NaNH2 ^ ^ H2/Pd-BaSQ4 ^y alkaline KMnQ4 ^ j
CH3CH,C-=-C-H
(ii)CH3CH2Br
Q.24 A biologically active compound, Bombykol (C ]6 H 30 O) is obtained from a natural source. The structure
of the compound is determined by the following reactions.
(a) On hydrogenation, Bomby kol gives a compound A, C 1 6 H 34 0, which reacts with acetic anhydride to
give an ester.
(b) Bombyk ol also reacts with acetic anhydride to give another ester, whic h on oxidative ozonol ysis
( 0 3 / H 2 0 2 ) gives a mixture of butanoic acid, oxalic acid and 10-acetoxy decanoic acid.
Determine the number o f double bonds in Bombykol. Write the structures o f compound Aand Bombykol.
Ho w many geometrical isomers are possible for Bombykol? j LIT 2002J
Q.25 If after complete ozono lysis of one mole of monomer of natural polymer giv es tw o moles of CH 2Q
andone mole of O = C - CH = 0 . Identify the monomer and draw the all-cis structure of natural polymer.
[IIT 2005]
Identify X and Y. [IIT 2005]
^Bansal Classes HYDROCARBON [34]
ANSWER KEY
EXERCISE-I (A)
Q.l B Q.2 A Q.3 A Q.4 D Q.5 A Q.6 A Q.7 C

Q.8 C Q.9 C Q.10 C Q. ll D Q.12 A Q.13 B Q.14 A
Q.15 B Q.16 B Q.17 D Q.18 B Q.19 D Q.20 B Q.21 B
Q.22 C Q.23 D Q.24 A Q.25 A Q.26 B Q.27 A Q.28 C
Q.29 B Q.30 B Q.31 C Q.32 A Q.33 D Q.34 A Q.35 B
Q.36 B Q.37 A Q.38 A Q.39 D Q.40 B Q.41 B Q.42 A
Q.43 B Q.44 B Q.45 B Q.46 A Q.47 C Q.48 B Q.49 A
Q.50 A Q.51 A Q.52 C Q.53 C Q.54 C Q.55 A Q.56 C
Q.57 C Q.58 C Q.59 C Q.60 A Q.61 D Q.62 A Q.63 A
Q.64 C
EXERCISE-I (B)
Q.l A,C Q.2 A,C Q.3 A,B,C,D Q.4 A,B,C,D

Q.5 B,C Q.6 A,B Q.7 A,B,C Q.8 A,B,C,D
Q.9 A,C Q.10 A,B Q.ll A,B Q.12 A,C
Q.13 B,C Q.14 B,D Q.15 A,C Q.16 A,B,D
Q.17 A,C,D Q.18 B,C,D Q.19 A,D Q.20 D
Q.21 B,D Q.22 A,C,D
Q.23 (A) 3,4 ; (B) 3,4 ; (C) 1, 2;(D)2 Q.24 (c) Q.25 (c)
Q.26 (d) Q.27 (a) Q.28 (A) 4; (B) 3; (C) 1; (D) 3,4
Q.29 (A)5,7 ; (B) 4,5 ;(C) 3 ; (D) 1,2,6 Q.30 (A) 4,7;(B)5,6; (C)3,4; (D)5,6 ; (E)2
EXERCISE-II
w
coo® co o
-D D- -H
Q.l (a) (b) +
DO- -H H- -OD
H BH, H HO
COO® COO®
CFL
C H 2 - C H 2 - C- H
O = CH
Q.2 CHL-C = CH ? Q.3 +
n_CH=i
CH=0 O = CH
C,HC C,H<
-OH OH- -H
Q.4 A + B are two enatiomers
OH- "H H- -OH
c2H5 C?H=
H D CH 7 NO 2
- CH O
Q.5 Q.6
-CHO
CH^NOt
Q.7 CH 2 = C H - C H 2 - C H 2 - C H 2 - N - C H 3
CH 3
Q.8 (i) C-C-C-C=C, (ii) C - C - C = C - C - C , (iii) C - C = C - C, (iv) C-C=C-C-C=C,
c c c
(v) ^
Q.9 a-pinene -> (A) = V ^ ^ B r , (B) = (C) = ^ / V ^ r

Br 0 H
Me Me
OH ONa
Q.10 (A) c _ c _ c _ c , (B) C - C - C - C, (C) C- C- C- C- O- C- C, (D) BrMg- C-C -C- C
(E) C-C-C-C-C-C-C-C-C,(F)C-C-C-C=C-C-C-C-C,
OH
Br
(G) C - C - C - C - C - C - C - C - CV(H) C- C- C- Cs C- C- C- C- C
Br
C-C C-C C-C
Q. ll (A) C - C = C - C - C = C - C , (B)cis C - C = C - C - C = C - C , ( C ) H O O C - C - C OO H ,
C C C C C
C-C
(D) H-C-COOH
i
c
Phv /H Ph- CH- Et

Q.12 (A)PhC S CMgx, (B)Ph-C=C-CH 2 Ar,(C) H / c = c
\ c H _ A r ,(D) ^
(E) Ph -CH =C H- Me trans, (F) Ph - CH - CH - M e (threo mix.), (G) Ph- COO H

I !
OH OH
(H) cold dil. KMn 0 4 , (1) HCO,H, (J) CF 3 CH 2 CH 2 Br, (K) / Q ^
Q.13 (i) 0 iv no
™ w ' r ' V N r " ' \ / ^ L > ( ) reaction
C0 2 ME I I N
Br
W(A)p h _l H ^ C H 2 _ B r ,(B)Ph-C,C^H 3
Q. 14 (i) II is faste r, (ii) unstable intermediate Q.25
O -CH3
C 1
/ I
Q.26 (A) Me CH 2 -C=C-OCMe, (B) CH2=C\ , ( Q CH 2 = CH - CH == CH - CH - CH ,
CI
Br OH
/
(D) <^JyC-CH3
\ Ii I I
, (E) CCI3 - C H - C H 3 (F) ^ J k c H 3 '
(G) A/ \/\A
0 0
EXERCISE-UI
H 13 C \
Q.l > CH-CH,OH
H3C/
Q. 2 (A) CH, (B) CH 3 (C) CH 3

I ' I I
HjC-CH-C^CHjCl H3C-CH-CH-CH3
I
CH^—CH—CH^ CH^ CI
(D) CH3 © CH 3 <F) CH3
I I I
CH--C-CHXH, C1CH,- CH-CHXH,
I H 3 C-C=CH-CH 3
CI (G) CH3COCH3 (H)
CH 3COOH
Q.3 (A) CHXHXH, (B) CHCHXH, (C) CH=CH-CH3
I
CH 2=C-CH ; CH 3 CHf-CCH^CH^ CH3 -CH -CHXH3
(D) CH 2 -CH=CH 2 (E) C^CHjCHj (F) CHXH^CH^
! I I
CHg-CH-CH^ CFL CH,-C=CH-CH 3 CH 3 -CH-CH=CH2
(G) CHXHXH,
H 3 C-C-CH 2 CH,
i
H
Q.4 (I) CH3 (J) CH3 CH3

I I I
CH3CH-C-CH3 CH 3-C- CH-CH3
I I I
I CH3 I
Q. 5 (A) CH3-C=CH-CH3 (B) CH2=CCH2CH3 (C)CH2=CHCH(CH3)2

I I
CH, CH,
Q.6
CH3
(A) CH3-CH-CH (B) CH^r-CH^-CH-CI^ (Q CH2=CH-CH-CH3
CH
s
CH, CH3
(D) CH3CH=C~CH3
I
CH3
Q.7 CH=CH2
I
(A) CH3-CH=CH-CH3 (B) :c=c (Q CH^-C* -H
I
CK^CH^ ]
Q. 8 (X) CH3-CC1"CH-CH3 (Y) CH2=C — CH-CH3 (Z) CH 3-C = C-CH3
CH3 CH3 CH3 CH3
Q.9 (A)PhCH(CH3)CH2CH3 (B)PhC(CH3)3
Q.10 OH
(A) CH-C HV-C -CH^ -CHX H, (B) CH3CH 2-C-CH2 CH2 CH3 (C) CH 3 CH 2 -C-CH,CH,
CH
2 CH3 O
(D) CH3 (E) CH3 (F) CHj
i I I
CH3-CH-C-CH2CH3 CH3CH-CH-CH2CH3 CHj-CH-CH-CHJ-C^
II
CH2 CH2OH CO,H
(G) CHJ-CH- C-CH 2 -CH 3

I II
CH3 0
Q.LL (A) C^CH^CH^-CHCH, (B) CH3CH,CsC-CH, (C) Cvclopentene
Q.12 CH3 CH3

I I
(A) CH 3 -C-C^CH (B) I^ C-C -OC " Na+
I I :
CHj CH3
CH, CHj
(C) H3 C-C-C=C^CH2 CH 2 CH 3 P) H,C-C-C=CH-CH2 CH 2 CH 3
CH, CH,

NOMENCLATURE OFORGANIC COMPOUND
Q .1 3 (A)[>-OC^j (B )[ > -C OO H ( C ) [ > -B r
Q. 1 4 (A) CH 3 - CH= CH-CH=CH -CH 3 (B) CH3CH2CH2CH=CHCH 3 (C) CH3CH 2CH 2CH 2-CH 2CH 3
(D) CH,CHO (E) CHO (F) CH3CH 2CH 2COOH
i
CHO
Q. 15 (A) CH3-CH=CH-CH-CH 3 (B) CH 3 -CH-CH-CH-CH3 (C) CH 3 -C=C-CH-CH 3

I I I
CH3 Br Br CH, CH3
(D) CH,-CH-CH -CH-CH, (E) CH3COOH (F) H 3 C-CH-COOH

i I I I
OH OH CH, C^
H
l
Q.16 CH3-C = C - C - C = C- CH 3
I I I
H H CH 3
Q. 17 CH,CHXH= CHCH,CH3
Q. 18 (A) CH 3 -CH= CH-C H=CH -CH3 , (B) CH 3 - C H 2 - C H = C H - C H 2 - C H 3 ,
CHO
(C) CH 3 - C H 2 - C H 2 - C H 2 ~ C H 2 - C H 3 , (D) CH3 CHO , (E) I , (F) CH 3 C H 2 COOH
CHO
Q.1 9 Isomer are : C^ C- C- C, C=C-C=C , C=C=C- C,
Q.20 23.7
EXERCISE-IV (A)
Q.l C Q.2 A,D Q.3 A Q.4 C Q.5 A
Q.6 D Q.7 A,C Q.8 D Q.9 A Q.10 D
Q.ll C Q.12 B Q.13 B Q.14 A Q.15 B
Q.16 D Q.17 A Q.18 B Q.19 B Q.20 B
Q.21 D Q.22 A Q.23 A Q.24 B
EXERCISE-IV (B)
Br
CH=CH-CH, (L,H-CH9-CH 3
CH 2 -CH-CH 3 ALC. KOH
Q.l CH, - C = C H - C H , Q .2 * F O
CH3
H
/ R
Q .3 CH -CH - C - C H = C H2 Q. 4 ,C = C
3 2
-H
I
CH3
C H
( 6 12)
Me Me CH 2 CH2
"Br + Br- -H
Q.5 Q.6 (E) CH , - C - CH
Br- "H H- -Br
Me Me
Br OH
Q.7 (a) (CH 3 -C H 2 ) CH - CH - C H 3 ; (b) ( CH 3 -C H 2 ) 2 C - C H - C H 3 ; (c) (C 2 H 5 ) 3 C-OH
Br
CH 3 CH 3 CH 3 CH 3 CH 3 CH 3
Q.8 C H 3 - C - C H - C H 3 ; ( Y ) C H 2 =C - C - C H 3 ; (Z) C H 3 - C = C - C H 3
CI
Q.10 (A)
< B >o 0
Q.ll (A)C H 3 - C H 2 - C H = C H - C H 2 - C H 3 (B) CH 3 CH 2 COOK
Q. 16 1 -> ozonolysis; 2 - » LiAlH 4 ; 3 -> H 2 S 0 4
Q.17 (4) —> HO-C 1 ; (5) CH 3 MgCl ; (6) -> t^ O / f f
Q. 19 (1) NaN"H2, (2) Me- I, (3) Hg S0 4 dil H 2 S 0 4
Q.2 0 higher electronegativity of sp carbon
CH,
-CH, CH,
Q.2 1 (i) CH 3 - C - C H 2 - CH 3 (ii) I
O-C2H6
Et
Et Et -OH
Z
Q.23 (X) —»Et-CsC-Et (Y)->H>C=C<H ( )^ H Z is meso so optically inactive.
-OH
Et
Q.2 4 B omby ko l :- HO -C - C - C - C -C -C -C -C - C - C = C -C = C - C - C - C
(A ) : - HO-tCH^ 5CH3 4 geometrical isomers are possible
CH 3
| H
Q.25 (a) CH 2 = C - CH = CH 2 (b) (CH2
Q .2 6 ( X ) I ^ J ,(Y) C H 3 - C - ( C H 2 ) 4 ~ C H = 0
CH,
<1
BANSAL CLASSES
CHEMISTRY
TARGET IIT JEE 2007
XI(PQRS)
llllllllllilllllilllll li|i|||||!ill||ll|||il||i;;:, ..,:|||lllllllllllllllll v
NOMENCLATURE
OF
ORGANIC COMPOUNDS
CONTENTS
EXERCISE-I
EXERCISE - II
ANSWER KEY
IUPAC
Nomenclature according to IUPAC system involves use of following terms:
(i) Word root: The word root represents the number of C atoms in parent chain.
No. of C atom W.R.
1 Meth Oct§fe>8
2 Eth Non3Jps>9
3 Prop. DecaSe 10
4 But UndetoSBsll
5 Pent Doded&L©12
6 Hex Tridecah©13
7 Hep
(ii) Primary suffix: Primary suffix is used to indicate saturation or unsaturation in carbon chain.
While writing name, primary suffix is added to word root.
Nature ofC chain Primary suffix
(1) Saturated C chain ane
(2) Unsaturated C chain
C=C ene
C=C yne
2 C=C diyne
(iii) Secondary suffix: Secondary suffix is used to indicate functional group in organic comp. It is added
primary suffix by dropping its terminal "e".
Prefix: The part of the name C appears before the word root is called prefix. Different prefixes are
used for dif categories of group as:
(a) Alkyl groups:
CH3-CH2-CH2 > 1-propyl
CH3-CH-CH3 j-CT^
CHj-CH^CH > 2-propyl
> 1-Butyl
CH3-CH2-CH-CH3 > 2-Butyl
CH, *
2-Methyl-l-propyl
CH, - CH - CH,
(b) In IUPAC system,for nomenclature some groups are not considered as functional group but
treated as substituent. These functional group are always indicated by prefixes instead of
secondary suffixes.
-N02 Mtro
-OR Alkoxy
-CI Chloro
-Br Bromo
-I Iodo
-F Fluoro
-N=0 Nitroso
-N02 Nitro
=N Diazo
"[250]
tBansal Classes NOMENCLATURE OF ORGANIC COMPOUND ~
(c) Iftwo different substituents are at same position from opp. ends, lowest no. is assigned in order
of their alphabets.
1 2 3 4 4 3 2 1
c-c-c-c c-c-c-c
I I I I
CI I CI Br
itvs H j o v v J ^ If more than two substituents & side'chains are present, the sum of their numbers should be
C4OYV6L VW r. a c lowest at the first preference irrespective of the nature of substituent or side chain. This is K/a
"VDOUU lowest sum rule.
S u t e S * ^ 7 6 5 4 3 2 1 1 2 3 4 5
Jvaue, ^ ^ C- C- C- C- C — C-C C- C- C- C- C
Se ri e s ^ l o ca m t s C H CH , CH , CI I CH , Br
0 c%a 3
CcwkiiHirfy Z™ " t y .
Jre^rm-s excê- * Inâsewheh starting loeant is lo ê rf ro m cfie sid£, then lowest sum rule is n6t obeyed.
CotvôW, -teawtyW,, t-b-C-d-C-C-C-t-t-C
Sashes sk.c&<ii4 | j j
CCYvicxS^ "VW. VcAAJ^ VVO. C7T\ C C C
^Vve. o c t e t s ;on. c^ 1st •
(iii) Arrangement of prefixes :
(a) Side chain or substituent group are added as prefix C its loeant in alphabetical order.
CH3-CH-CH-CH,
2-bromo, 3-chlorobutane
CI Br
H , C - C H - C H - C H 2 - CH 3
3 chloro, 2-methyl butane
CH3 CI
(b) If more than one similar alkyl group or substituents are present terms, tri like are used.
CH 3
I
H,C — C — CH-,
• | - 2,2-dimethyl propane 2;3-dimethyl
CH 3
(c) In case side chain is also branched, it is also numbered form carbon atom attached to main chain
& is generally written in brackets.
3 4 5 6 7
CH, - CH 2 — CH — CH2 — CH 2 — CH 2 — CH 3
2 C H- C H 3
1 CH 3
tBansal Classes NOMENCLATURE OF ORGANIC COMPOUND
3-ethyl-2-methyl heptane
1 2 3 4 5 6 7 8
CH 3 - CH - CH2 - CH 2 - CH - CH 2 - CH 2 - CH 3
I I
CH 3 1 CH-C H 3
2 CH3
2-methyl-5-(l-methyI ethyl) octane
The use ofiso & related common prefixes for describing alkyl group as long as these are not further
substituted are also allowed by IUPAC nomenclature. While writing name in alphabetical order prefixes
iso & neo are considered to be part of fundamental name of alkyl group. However sec. & tert are not
considered to be part of fundamental name.
CH3-CH-CH2CH3
c-c-d-c-c-c-c-c-c-c
-CP(CH 3)# _ - - - -
For unsaturated hydrocarbon:

(i) Select the longest possible carbon chain having maximum no. ofunsaturated carbon atoms or max. no.
of double or triple bonds, even ifpuor rule is violated.
c-c-c-c-c-c
Ifl i - .
c
(ii) Lowest no. is assigned tofirstunsaturated carbon even if prior rule is violated.
1 2 3 4 5 6 7
CH 3 - CH 2 - HC = CH - CH 2 - C-i
C - CH3
CH,
A
3
(Si) If double & triple bonds are at same position from either ends, lowest no is assigned to double bond
1 2 3 4
c=c-c-c=c
(iv) If both alkene & alkyne group are present, the org. compound is named as derivative of alkyne rather
than alkene.
CH 3 -€H=CH-C=CH
Pent-3-en-l-yne
In some cases all the double & triple bonds present in molecule can't be included in longest chain. In such
cases following prefixes.
CHJ = CH 3-CH=
Methylene Ethylidene
CH=C- CH2 =CH-

Ethynyl Ethenyl
Forfunctional groups :
(i) Select the longest possible carbon chain having max. no. of functional even if prior rules are violated.
C-C- C-C- C-OH

I I
OH C
I
c
(ii) The carbon atom of functional group is to be included in deciding the longest carbon chain.
C-C-CN 3 carbon chain
C-C-C-CHO 4 carbon chain
(lii) The lowest no is assigned to functional group even if prior rules are violated.
| 4 3 2
CH3
CH,
5 4| 3 2
CH 3 -C-CH 2 -CH-CH 3
I I
CI
1
(iv) The order of numbering a carbon chain, thus follows the order:
(a) Functional group
(b) Unsaturation
(c) Substituents & side chains

7 6 5 4 3 2 1
c=c-c-c-c-c-c
I
OH
1 2 3 4 5 6 7
c=c-c-c-c-c-c
I
OH
(v) If more than 1 functional group; then choice of principal functional group is made on the basis following
order of preference:
0 0 0 o o
I! II II II II
Carboxylic acid > S0 3 H > - C - O - C - > - C - O R > - C - 0 C 1 >
> aldehyde > Ketone > alcohol > thiols > amines > ene > yne > halo > -O R
faBansal Classes NOMENCLATURE OF ORGANIC COMPOUND [6]
Q.9 The IUPAC name of compound C H 3 - C - C H - C H - C H - C H 3 is:

I ! I
CH 3 CHOCH 3
(A) 3,5-Dimethyl-4-Formyl pentanone (B) 1 -Isopropyl-2-methyl-4-oxo butanal

(C) 2-Isopropyl-3 -methyl-4-oxo pentanal (D) None of the above
HO - C = O CH3
I I
Q.10 The IUPAC name of compound CH3 - C = C — C - H is:
I I
NH 2 CI
(A) 2-amino-3-chloro-2-methyl-2-pentenoic acid

(B) 3-amino-4-chloro-2-methyl-2-pentenoic acid
(C) 4-amino-3-chloro-2-methyl-2-pentenoic acid
(D) All ofthe above
Q.LL The IUPAC name ofthe structure is:

CH-C]
I I
HOOC COOH
(A) 3 -amino-2-formyl butane-1,4-dioic acid (B) 3 -amino-2,3 -dicarboxy propanal
(C) 2-amino-3 -formyl butane-1,4-dioic acid (D) 1 -amino-2-formyl succinic acid
Q.12 C 4 H 6 0 2 does not represent:

(A) A diketone (B) A compound with two aldehyde
(C) An alkenoic acid (D) An alkanoic acid
Q .13 Esters arefiunctionalisomers of:

(A) Hydroxy aldehyde (B) Ketone (C) Diketone (D) Diols
Q.14 How many carbons are in simplest alkyne having two side chains?
(A) 5 (B)6 (C)7 (D)8
Q.15 Which of the following is not correctly matched:

(A) Lactice acid CH3 - CH - COOH
I
OH
(B) Tartaric acid HO- CH -C OO H

I
HO-CH-COOH
(C) Pyvaldehyde CH3C(CH3)2CHO
CH,
3
I
(D) Iso-octane
I I
CH 3 CH3
fa Ba ns al Classes NOMENCLATURE OF ORGANIC COMPOUND [8]
Q.16 Which of the following pairs have absence of carbocyclic ring in both compounds?
(A) Pyridine, Benzene (B) Benzene, Cyclohexane
(C) Cyclohexane, Furane (D) Furane, Pyridine
Q.17 The commerical name of trichloroethene is:

(A) Westron (B)Perclene (C)Westrosol (D)Orlone
Q.18 The compound which has one isopropyl group is:
(A)
(C) 2,2,3,3 -tetramethyl
2,2,3 -trimethyl pentane
pentane (B)
(D) 2,2-dimethyl pentane
2-methyl pentane
Q.19 How many secondary carbon atoms does methyl cyclopropane have?
(A) None (B)One (C)Two (D) Three
Q.20 The IUPAC name ofthe compound CH, - CH - CH is:

I I I
OH OH OH
(A) 1,2,3-tri hydroxy propane (B) 3-hydroxy pentane-1,5-diol
(C) 1,2,3-hydroxy propane (D) Propane-1,2,3-triol

Q.21 As per IUPAC rules, which one of the following groups, will be regarded as the principal functional
group?
(A) -C=C- (B)-OH (C) - C - (D) - C - H
II II
o o
Q. 22 Which ofthe following is thefirstmember of ester homologous series?

(A) Ethyl ethanoate (B) Methyl ethanoate (C) Methyl methanoate (D) Ethyl methanoate
Q.23 The correct IUPAC name of2-ethyl-3-pentyne is:

(A) 3 -methyl hexyne-4 (B) 4-ethyl pentyne-2 (C) 4-methyl hexyne-2 (D) None of these
CI CH2CH3
Q.24 IUPAC name for the compound yC=C<^ is
h 3 C/ \
(A) E-3 -iodo-4-chloro-3 -pentene (B) E-2-chloro-3 -iodo-2-pentene
(C) Z-2-chloro-3 -iodo-2-pentene (D) Z-3-iodo-4-chloro-3 -pentene
Ph
Q.25 The IUPAC name ofthe compound is CH3 - CH - CH - NH2
I
CH3
(A) 1 -amino-1 -phenyl-2-methyl propane (B) 2-methyl-1 -phenyl propane-1 -amine
(C) 2-methyl-1 -amino-1 -phenyl propane (D) 1 -isopropyl-1 -phenyl methyl amine
tBansal Classes NOMENCLATURE OF ORGANIC COMPOUND ~ "[9]
q 34 c c h 3
© @ c > @ '
Number of secondary carbon atoms present in the above compounds are respectively:
(A) 6,4,5 (B) 4,5,6 (C) 5,4,6 (D) 6,2,1
Q. 3 5 The IUPAC name of acetyl acetone is:

(A) 2,5-Pentane dione (B) 2,4-Pentane dione (C) 2,4-Hexane dione (D) 2,4-butane dione
Q. 3 6 When vinyl & allyl are joined each other, we get

(A) Conjugated alkadiene (B) comulative alkadiene
(C) Isolated alkadiene (D)Allenes
Q.37 Glycerine is:

(A) Propane triol-1,2,3 (B) Propylene trialcohol
(C) Propyl glycol (D) Hydroxy methyl glycol
0H R^ YCH2CLI,OH
O and (b)l^J
True statement for the above compounds is:
(A) (a) is phenol while (b) is alcohol (B) Both (a) and (b) are primary alcohol
(C) (a) is primary and (b) is secondary alcohol (D) (a) is secondary and (b) is primary alcohol
Q.39 IUPAC name will be CH2 - CH - CH2

I ! !
CN CN CN
(A) 1,2,3 -Tricyano propane (B) Propane trinitrile-1,2,3
(C) 1,2,3-cyano propane (D) 3-cyano pentane-1,3-dinitrile
Q.40 A substance containing an equal number ofprimary, secondary and tertiary carbon atoms is:
(A) Mesityl Oxide (B) Mesitylene (C) Maleic acid (D) Malonic acid
Q.41 IUPAC name of

or*
(A) But-2-ene-2,3-diol (B)Pent-2-ene-2,3-diol
(C) 2-methylbut-2-ene-2,3-diol (D) Pent-3-ene-3,4-diol
Q 42 The IUPAC name of BrCH 2 -CH-CO-CH, - CH2CH3is:

I
CONH2
(A) 2-bromo methyl-3-oxo hexanamide (B) 1 -bromo-2-amino-3 -oxo hexane

(C) 1 -bromo-2-amino-n-propyl ketone (D) 3 -bromo-2-propyl propanamide
tBansal Classes NOMENCLATURE OF ORGANIC COMPOUND ~ "[11]
Q.43 IUPAC name of is:
(A) 5-methyl hexanol (B) 2-methyl hexanol

(C) 2-methyl hex-3-enol (D)4-methylpent-2-en-l-ol
Q.44 The IUPAC name of CH3 CH2 - N - CH2CH3 is:

I
CH3
(A) N-methyl-N-ethylethyl amine (B) diethyl methyl amine
(C) N-ethyl-N-methyl ethyl amine (D) methyl diethyl amine
Q.45 The molecular formula of the first member of the family of alkenynes and its name is given by the set
(A) C3H2, alkene (B) C5H6, l-penten-3-yne
(C) C6Hg, l-hexen-5-yne 0 (D) C4H4, butenyne
CH 2 -C-OH
c x< m
Q.46 The IUPAC name of compound | COOH
CH2-COOH
(A) 1,2,3 -tricarboxy-2,1 -propane (B) 3-Carbox-3-hydroxy-l,5-pentane dioic acid
(C) 3 -hydroxy-3 -Carboxy-1,5-pentane dioic acid (D) None
Q.47 The IUPAC name of the compound: \ q i_ch 3

(A) Propylene Oxide (B) 1,2-Oxo propane
(C) 1,2-Epoxy propane (D) 1,2-Propoxide
Q. 48 One among the following is the correct IUPAC name of the compound
H
I
N
(A) N-Formyl aminoethane (B) N-Ethyl formyl amine
(C) N-Ethyl methanamide (D) Ethylamino methanal
Q. 49 Which among the following is the correct IUPAC name of isoamylene:

(A) 1 -Pentene (B) 2-Methyl-2-butene (C) 3 -Methyl-1 -butene (D) 2-Methyl-1 -butene
•OH
Q.50 The IUPAC name of 11
<
| S is
CH3
(A) 3 -Methyl cyclo-1 -butene-2-ol (B) 4-Methyl cyclo-2-butene-1 -ol

(C) 4-Methyl cyclo-l-butene-3-ol (D) 2-Methyl cyclo-3-butene-l-ol
Q. 51 Which ofthe following is a heterocyclic compound

HC = CH ^ HC = COOH HC = C H ^ HC = CH
(A) I >S (B) I (C) I > C H 2 (D) I C=0
V
HC = CH / HC = COOH HC = C H / HC = CH
Q. 52 The number ofprimary, secondary and tertiary amines possible with the molecular fomula C3HgN is:
(A) 1,2,2 (B) 1,2,1 (C) 2,1,1 (D) 3,0,1
Q. 53 The IUPAC name of C6H5CH=CH-COOHis:

(A) cinnamic acid (B) 1 -phenyl-2-carboxy ethane
(C) 3 -phenyl prop-2-enoic acid (D) dihydroxy-3 -phenyl propionic acid
Q.54 The IUPAC name o f i ^ V CH = CH - CHCH2CH is:

U
c k
(A) 1 -cyclohexyl-3 -methyl-1 -pentene (B) 3 -methyl-5-cyclohexyl-pent-ene

(C) 1 -cyclohexyl-3 -ethyl-but-1 -ene (D) 1 -cyclohexyl-3,4-dimethyl-but-1 -ene
Q. 55 The IUPAC name of CH - C - O - CH2 - C - OH is:

il II
O O
(A) 1 -acetoxy acetic acid (B) 2-acetoxy ethanoic acid
(C) 2-ethanoyl oxyacetic acid (D) 2-ethanoyl oxyethanoic acid
Q 56 The IUPAC name of 0,NH

N- \0)~
_ CHOis:
s
OCH 3
(A) 2-methoxy-4-nitro benzaldehyde (B) 4-nitro anisaldehyde
(C) 3-methoxy-4-formyl nitro benzene (D) 2-formyl-4-nitro anisole
Q. 57 The IUPAC name C - CH3 is:

(A) phenyl ethanone (B) methyl phenyl ketone
(C) acetophenone (D) phenyl emethyl ketone
CH3(CH2)4 Cll 2 (CH2)7COOH

Q.58 The IUPAC name of .C=C. ,C=C. is:
X x
IK H W H
(A) cis-cis-9,12-octadecan dienoic acid (B) cis-trans-9,12-octadecan dienoic acid
(C) 9,10-octa decadienoic acid (D) 9,14-octa decadienoic acid
Q. 5 9 The suffix of the principal group, the prefixes for the other groups and the name of the parent in the
structure
CH3 CI 0 0
(A) -oic acid, chloro, hydroxy, oxo, methyl, 4-heptene
(B) -oic acid, chloro, hydroxy, methyl, oxo, 4-heptene
(C) -one, carboxy, chloro. methyl, hydroxy, 4-heptene
(D) -one, carboxy, chloro, methyl, hydroxy, 4-heptene
faBansal Classes NOMENCLATURE OF ORGANIC COMPOUND JlOJ
EXERCISE - II
Q.ll
Q.l
O 0
Q.12
Q.2
COOH
Q.13
Q.3 02N Q.14
Q.4 Q.15
Q.16
q.5
CH2-CHCH3
Q.17 \ Q /
Q6 / \ / \
Give the IUPAC names for each ofthefollowing :
q.7 Q.18
Q.19
Q.8
OH CH2CH2CH2CH3
Q.20
Q.9
C H 3^ ^ C H ( C H3 ) 2
Q.21
CH,
Q.10 Q.22 |^YC2h5
faBansal Classes NOMENCLATURE OF ORGANIC COMPOUND JlOJ
CH, BivjCH,
Q.34
Q.23
CH3 O
C-CH 3
^ k . C - O C H
Q.24
a
3
CH,
Q.35
CH3 .CH .
Q.25 J
CH, Q.36
CH2CH2CH=CH2
Q.26
Q.37
Q.27 Q.38
0<1
C-CH2CH3
Q.28 Q.39
ff Q.40
C-OC2H5
Q.29
Q.41
Q.30
Br
Q.42
CHO
Q.31
OH
/CI
Q.43
A / C H O
Q 32
c xBr N
Q.44
-OH
OH 9H3
CHCH2CH 3
O
Q.33 Q.45
COOC2H 5
NH 7
Q.46 CH 3
(b) H 3 C - N - C H - C H 2 C H 3
CH 3 CjHJ
Q.47
Q.56 Write IUPAC name of succinic acid
.-OH
Q.48 / \—CsCH
r>
O CI
II I
Q.49 CH- - C - CH- - CH - CH,
0 H
Q.50 O \
\ NH 2
Q.51 K Y V
OC 2 H 5
CH=CH-CH-CH=CH 2
Q.54
Q. 5 5 Write IUPAC Name offollowing:
Me
Me
(a) Me = methyl group
Me
ANSWER KEY
EXERCISE -1
Q.l B Q2 A Q.3 B Q.4 C Q5 B Q.6 B Q.7 C

Q.8 C Q.9 C Q.10 B Q. ll C Q.12 D Q.13 A Q.14 B
Q15 D Q.16 D Q.17 C Q.18 D Q.19 C Q.20 D Q.21 D
Q.22 C Q.23 C Q.24 C Q.25 B Q.26 B Q.27 C Q.28 B
Q.29 D Q.30 B Q.31 B Q.32 B Q.33 A Q.34 A Q.35 B
Q.36 C Q.37 A Q.38 D Q.39 A Q.40 B Q.41 B Q.42 A
Q.43 D Q.44 C Q.45 D Q.46 B Q.47 C Q.48 C Q.49 C
Q.50 B Q.51 A Q.52 C Q.53 C Q.54 A Q5 5 D Q.56 A
Q.57 A Q.58 A Q.59 B Q.60 D Q.61 D Q.62 C Q.63 C
Q.64 B Q.65 D Q.66 A Q.67 A
EXERCISE - II
Q.L CH, - CH - C - CH 2 - OH Q.8 CH =CH-C-CH2

! II I
CH2-CH3 O OH
2-ethyl-2-butene-1 -ol 1 -Hydroxy-3 -Butene-2-one
Q.2 CH3-CH2-CH-CH2-CH2-CH2 CH
3 CH3-CH-CH3
Q.9 CH3 - CH 2 - CH - CH - CH,

4-Ethyl octane
CH 3
Q.3 CH = CH - CH,
3-Ethyl-2,4-dimethyl pentane
NO, OH
3 -nitro-2-propene-1 -ol
Q.10 CH7 = C - CH, - CH - CH ,
OH O
I II 2-isopropyl-4-methyl-1 -pentene
Q.4 CH,2 = CH - CH - C - C = CH
6 5 4 3 2 1
Q.ll CH,-CH 2 CH,

4-hydroxy-5-hexene- lyne-3-one I
C=C-CH
l-Hexene-3-yne
Q.12 CH,-C-CH2-C-CH3
iCN
II II
2-Formyl pentane nitrile o o
Q6 CH2 = CH - CH2 - OCH, 2-4, pentane dione
1 -Methoxy-2-prop ene
Q.13 Cyclopropanecarboxylic acid
Q.7 3 -methyl-1,4,6-Heptatriene
Q.14 Cyclopropane carboxylic acid Q.39 spiro(4.5) decane
Q.15 1,3,5-cyclohexatriene Q 40 Bicyclo (2.2.1) heptane
Q.16 1,3-cyclobutadiene Q.41 Bicyclo(4.4.0) decane
Q.17 1,2-epoxy propane Q.42 Bicyclo(2.2.1) heptane
Q.18 2,2,6,7-tetramethylocatane Q.43 8-chloro bicyclo(4.2.0) oct-2-ene
Q.19 3-ethyl-4,6-dimethyloctane Q.44 2-cyclepenten-l-ol
Q. 20 Butyl cyclohexane Q.45 2-carbethoxy cyclopentanone
Q.21 3 -isopropyl-1 -methylcyclohexane Q.46 Bicyclo (3.1.0) hexane
Q.22 2-ethyl-1 -methylcyclopentane Q.47 Cyclohex-2-en-1,4-dione
Q.23 Methyl enyl cyclohexane Q.48 2-ethynyl cyclohexanol
Q.24 Isopylidenecyclopentane Q.49 4-chloro-1 -cyclopentyl pentane-2-one
Q.25 1,3,4-dimethyl-1 -cyclobutene Q.50 1 -Amino methyl-2-ethyl cyclohexanol
Q.26 1 -(3 -butenyl) cyclopentene Q. 51 1 -propyl-4-isopropyl-1 -cyclohexene
Q.27 1,2-diethenyl cyclohexene Q. 52 2-(P-keto cyclohexyl) propanoic acid
Q.28 1-cyclohexyl-l-propanone Q. 53 3-ethoxyl-1 (1 -nitrocyclohexyl)-hexe-4-one-1
Q.29 Ethyl cyclohexanecarboxylate Q.54 l,3-diphenyl-l,4-pentadiene
Q.30 4-Bromo-2-ethyl cyclopentaneone Q.55 (a) 5,6-diethyl-3 -methyl-dec-4-ene

(b)N,N,3-trimethyl-3-pentanamine
Q. 31 3-(l -hydroxyethyl)-5-methylheptanal
Q.56 Butane-1,4-dioic acid
Q.32 6-Bromo-2-oxocyclohexanecarbaldehyde
Q.33 3-amino-2-sec-butyl-5 -cyclohexen-1 -ol
Q.34 2-bromo-2-methyl cyclopentanone
Q.35 Methyl-2-methoxy-6-methyl-3- cyclohexene

carboxylate
Q.36 Bicylo(2.2. l)heptane
Q.37 9-methyl bicyclo(4.2.1) nonane

Dokumen.tips Bansal Classes Organic Chemistry Study Material for Iit Jee 1

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ACIDITY. BASICITY. H-BONDING & TAUTOMERISM

(a) CH 3 CH 2 -N-CH : (b) CH 3 -C® (C)(C6H5)3P:

( d) :Brf *(e) (CH3)3B (f) m

Q.5 CHjCHjMgBr + CH3C = CH >A +B

(A) CH 3 O : +C H 3 -CI: - > C H , -• O

(b) CH3-O-CH3 + :O- H—> CH 3 -O: +C H^ -P -H

(d) CH 3 - N H 2 + CH 3 - CH 2 - CI: —- > CH3 - N H 2 - CH 2 CH 3 + :CI:

(e) (CH 3)3CC1 + A1C13 > (CH 3)3<?H^A1C14

CH3 - c - CH3 + H 2SO4

Q.10 Methyllithium (CH 3Li) is often used as a base in organic reactions.

19 Explain whic h comp ound is the wea ker base.

Q. 20 Rank the following amines in increasing basic nature.

(i) (ii) (iii) (iv)

Q. 22 Arrange the basic strength of the following compounds,

^,-Q. 14 Arrange the following compounds in order of increasing basicity.

(ii) Br-CH 2-CH 2-CH 2-OH MgBr-CT^-CH^CH^OH f

(ii) glutamic acid : H 0 2 C \ ^ \ ^ C O O H . 2 ]9> 4 25, 9.67

(a) C ^ J ' (^O J ' cy cl°hexane carboxylic acid.

^b) 1-butyne, 1-butene, butane

NH2 NH-C 6 H 5 NH2

Q.2 3 Set the followin g in increasing orde r of pk b :

J® CH 3NH2 , ( CH 3 ) 2 N H, (CH3 ) 3 N, NH 3 [In aqeous medium ]

(i) (ii) (iii)

^Jy) CH3COOH, N 0 2 - C ^ - COOH, CH3 - C - CH 2 - C - OH

^ fafff CH O-C HL- CHO , C H 3 - C

Q. 27 Draw a mechanism for this reaction.

(i) (ii) (iii)

(b) [QJ CH 2 =CH-CH2 C0 2 H CH ^ CO . H

(i) (») <*)

x-(¥29 Explain which is a stronger acid.

^ a ) CH3CH3 BrCt^NO,, CH3 - C - CH3 & CH3 - C - CH2CN

^Jb) CH3 - CH2 - CH2 - OH or GH3 - CH = CH - OH

Which is a stronger base? & Why.

TheKaofphenylaceticacidis 5.2 x 10~5, and the pKa of propionic acid is 4.87.

y~CH 2-C-QH C H 3 -C H 2 -C-OH

phenyiacetic acid,5 propionic acid,

< Q - C H 2 C O O ° +CH3CH2COOH <^y~CH 2 C O O H + CH3CH2COO®

Q.46 Which ofthe following system show H-bonding during tautomerism.

(I) (nf C"3 (1) N "2 (J ^NH

yjtf.51 In each ofthe following pairs which is more stable:

d#52 In each ofthe following pairs which is less stable:

Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [10]

J * ) C H 2 - CHO and CH 3 - CHO

(c) [OJ CHO and[OJ^ CHO

(§ Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [11]

O ^ C P andCP J d ) h > = 0 and h > 0

(d) CH3CN (e) C \

8 Which ofthe following compounds can not exhibit tautoimerism:

(d) Ol I OJ (e) CH3 - NO

Q. 66 Isatin was thefirstcompound to show tautomerism.

JSC (0 <TI> 6 A(HI) (IV)

( S | Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [14]

Q. 73 % enol content of acetylacetone in following solvents is found as:

Explain the observation.

Q.51 (a) 2; (b) 2; (c) 1; (d) 2; (e) 1

4g Bansal Classes Q. Bank on Acidity, Basicity, H-Bonding & Tautomerism [16]

ALCOHOL & ETHER

Q. 1 Which of the following reaction is called as 'Bouveault-Blanc reduction'

Q.2 Glycol on treatment with PI3 mainly gives-

Q.3 Acrolein is formed when glycerol is heated w ith-

Q. 4 Glycerol on treatment with oxalic acid at 110°C forms-

Q. 5 If the starting material is 1-methyl-1,2-epoxy cyclopentane, of absolute configuration, decide which

Q. 7 In the following reaction,finalproduct is