o

Exercise
Q.l Number of required 02 mgj/for complete combustion of one mole of propane-
(AP ...jIfJ 54 (C) 16 (D) 10

Q.2 How much volume of ~r ""be needed for complete combustion of 10 IiI.of ethane-
(A) 135lic ~'~'5Iit (C) 1751il. (D) 205 lit.

Q.3 Whenn-butane is heated in the presence ofAICI)/I-ICI it will be converted i;»er-

(A) Ethane (B) Propane (C) Butene . '{B) Isobutane

QA The reacting species of ale. KOH is-

(A) OW (B) OR+ (D) RO-
Q.5 The product of reaction between one mole of acetylene and two mole ofHCHO in the presence of
Cu2C12-
(A) HOCH2 - C",C - CHpH (B) H2C = CH- C"'C - CH20H
(C) HC '" C - CH20I-l (D) None of these

Q.6 During the preparation of ethane by Kolbe's electrolytic method using inert elcctrodes thc pH Oflhc
electrolyte -
(A) Incrcases 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.7 Ethylene fomls ethylene chlorohydrin by the acti~ - .

(A) Dry HCl gas 1.( ry chlOrine gas
(C) Solution of chlorine gas in water (D) Dilute hydrochloric acid

Q.8 Anti-Markownikoff's addition ofHBr is not observed in-

(A) Propene v(l3) But-2-ene (C) Butene (D) Pent-2-ene

Q.9 Which alkene on heating with alkaline KMn04 solution gives acetone and a gas, which tlUllSlime water
milky-/
(A) 2-Methyl-2-butene L{B)Isobutylene
(C) I-Butene (D) 2-Butene

Q.lO B (Lindlnr R-C",C-R Nn/NH) A

A <yKl13 are geometrical isomers (R-CH=CH-R)-
~)A is trans, B is cis (B) A and B both are cis
(C) A and B both are trans (D) A is cis, B is trans

Q.II Which is expected to react most readily with bromine-

(A) CH)CI-I2CH) ,(B) CH2=CI-12 (C) CI-I",CI-I

Q .12 By the addition of CO and Hp on ethene, the loll owing is obtained-

(A) Propanoic acid (B) Propanal (C) 2-Propenoic acid (D) None of the above

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 •
Q.13 An alkyne C7H1Zon reaction with alk. KMn04 and subsequent acidification with HCI yields a mixture
CH,> -CHCOOH
of I + CH)CHZCOOH. The alkyne is-
. CH) /
(A) 3-Hex)11e \-$) 2-Methyl-3-hex)11e
(C) 2-Methyl-2-hexyne (D) 2-Methyl-2-hexene

Q.14 A compound (CsHs) reacts with ammonical AgNO) to give a white precipitate and reacts with excess of
KMn04 solution to give (CH3)zCH-eOOH. The compound is-
(A) CHz=CH-CH=CH-CH) (B) (CH))zCH-C",CH
(C) CH)(CHz)zC"'CH (D) (CH))zC=C=CH2

Q.15 Which of the following reagents cannot be used to locate the position of triple bond in CH)-C",C-eH)
(A) Br,- (B) O., ~u;+ - (D) KMn04

f /I

,
•!
'-C-CC_c
i A and B are-
(A) alcoholic KOH and NaNH2 (B) NaNH2 and alcoholic KOH
(C) NaNHz and Lindlar (D) Lindlar and NaNH2
I

BHJ THF
Q.18 B ( . HgSO,lH,SO, ) A
H,O,. ow
Aand B are-

/
-JA) CH)CH2CHO,CH)
°II
-C-CH)
°II
(B) CH) -C-CH) CH)CHZCHO

(C) CH)CH2CHO (both) (D) CH) -C- CH) (both)

II
°

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 (D) none is correct

Q.20 CH2=CH-CH=CH2 CCI]Br) product. The major product is-

(A) Br-CH2-CH=CH-CH2-CCI) (B) CI-I2 = CH- CH -C1-I2 - CCI)

I
Br
(C) CH2 =CI-I-C1-1-CH2 -Br (D) None is correct
I
CCI)

Q.21 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) 33.6 L (D) 44.8 L
Q.22 Dehydration of2, 2,3,4, 4-pentamethyl-3-pentanol gave two alkenesAand B.ll1e ozonolysis products
of Aand Bare-
o
II
(A) Agives (CH)))C-C-C(CH))) and HCHO

o
. II
Bgives CH) -C-CH2 -C(CH))J and HCHO

o
II
(B) Agives (CH)))C-C-C(CH))) and HCHO

o CH)

Bgives CH) -~-t-C(CH))) and HCHO

I
CH)

o
(C) A gives (CH)))C-~-CH(CJ-l))2 andJ-lCHO

o
II
Bgives (CH))-CH2 -C-C(CH))) and CJ-l)C1-12CI-IO
None of these
NH4CI
Q.23 CJ-l",CH Cu,C1, ) product

Pr~ctis-
...v0Cu-C",C-Cu (B) CH2=CH-C",CH (C) CJ-l",C-Cu (D) Cu-C",C-NH4

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, -
( \
C
( c.
':1
"

CH] CH]
I I
Q,24 CH] - C = CH - C - CH] NaIO,/KMnO,) products, Products are:-
I
CH]

o
II
(C) e:l] - C - OH , (CH])]C-COOH (D) None is correct

o
II
Q,25 Alkene A O,IH,O) CH] -C-CHJ + CH]COOH + CH] -C-COOH
, II
o
A can be:-
C(CH])2
CliCli, CH
II /] II
= HC l- CH]
I
A) J-IrC-CIi=C" (B) CH] - C - CH
CH]
~ Both correct (D) None is correct

0
Q,26

'h
reagent R, reagen. R I

HO OH HO Oli
R1 and R2 are -
I ,

(A) Cold alkahne KMnO 4' OsO /HP2 ~ Cold alkaline KMn04; HCOJH
(C) Cold alkaline KMn04, CH]-O-O-CH] (D) C6HSCO]H, HCO]H " ,

CH]
I
H-C
Q,27 II alkaline KMnO, ) A, which is true about this reaction?
H-C
IbH J

(A) A is meso I, 2-butan-di-{]1 formed by syn addition

(E) A is meso I, 2-butan-di-ol formed by anI! addition
(C) A is a racemic mixture of d and I, I, 2-butan-di-{]1 fOl1l1edby anti addition
(D) A is a racemic mixture of d and 11 ,2-butan-di-{]1 fOl1l1edby syn addition

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 0=0 + CH]MgBr H1O' lA Con.H2S04
l B O,IB,O/Zn lC
A, Band Care -
A B C

(A)
H H]
c
3 c5 e5 HO
HaCH] 0
(B)
c5 6HCHO
(C)
HOH]
c5 6«0 CHO
CH]
(D) "a'"'
e5 00011
Q.29
070=0
Acan be-
(A) Conc. H2SO4 (B) alcoholic KOH (C) Et]N (D) t-BuOK

Q.30 BrCH2-CH2-CH2Br reacts with Na in the presence of cther at 100°C to produce-,

CH,-CH
,,-/ 2
(C) CH (D)AIl of these
2
Q.31 Which has least beat ofbydrogenation-

(A)/ ~/r==,/ (D) "::===

Q32
.
v. H]
_(~I)_Hg~(_OA_c~),~/_H~,O_I_TH_F-+
(2)NaSH,/N.OHIH,O
lA.Ais-
/

Q.33 CH]~H=CH-CH] ~
(B)
a II
OH

product is Y (non-resolvable) then X can be-

cis
(A) Br2 water (B) HCOlH
(C) Cold alkaline KMn04 (D) all of the above

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 I

Q.34 Electrophilic addition reaction is not shO\m by

(A) CH2 =C- CH3 and Br2 (B) CH=CH2 and HO-CI
I
CH,
.'
I

Q.35 A mixture of CH4, C2H4 and C2H4 gaseous are passed through a Wolfbottle containing ammonicaJ
cupbus chloride. The gas coming out is I

(A) Methane . (B) Acetylene

I
(C) Mixture of methane and ethylene (D) original mixture

Q.36 Which reagent is the most u.seful for distinguishing compound I from the rdt of the compounds
CH3CH2C=CH CH3C=CCH3 CH3CH2CH2CH3 CH3CH=CH2
I II III N
(A) alk. KMn04 (B) Br/CCI4 (C) Br/CH3COOH ~AJ11monicaIAgN03
I CHCOOH I
Q.37 CH2=CH-CH=CH, + II ~ product X by reaction R. X and Rare
- CHCOOH

(A)
ce
I
COO]'1

COOI.I
COOH
DielsAJder (B)
ce
I
OOH

CCOOH
COOH
I

Friedel.Crafts

(C) @(
0
, COOH
DielsAlder
.
(D)
@r
0 COOH
Friedel.Crafts

, I

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 Exercise 2
1. An organic compound (A) (C,Hs) on hydrogenation gives compound B(C,Hll). Compound A on
ozonolysis gives Formaldehyde & 2 keto propanal. Deduce the structure of compound A.

2. An organic compound A of vapour density 49.5 gave a dihydric alcohol (B) on treatment with moist
silver.oxide but an alkene (C) on hcating with zinc dust. Identify A, B & c. Give IUPAC name of
the compound obtained by ozonolysis.

3. An alkanol (A) forms an alkene (B) on heating with concentrated H,SO, (B) is allowed to react
with Br, water & the product is dehydrogenated with alcoholic KOH giving a compound (C). C
forms D when hydrolysed with dilute H,SO, in presence of dilute HgSO,. D, not a ketone can also
be produced by dehydrogenation of A. Identify A, B, C & D & explain the reaction.

4. An organic compound (A) C,H,Br which readily decolourises Br, water & KMnO, solution gives
(B), C,HIIBr on treatment with Sn/HCI. The reaction of A with NaNH, produce C with evolution
ofNH). C neither reacts with Na nor forms a any metal acetyl ide but reacts wi'th Lindlar catalyst
to give D & on reaction with Na/liq. NH) produce E. Both the compounds D & E arc isomeric.
Give structures of A to E with proper reasoning.

5. When 1,4 hexadiene 301 is dissolved in H,SO, it is completely converted into 3, 5 hexadiene
2-01. How do you account for this.

6. A compound of the molecular formula C,H" has three isomers X, Y & Z. Monochloro derivative of
X yield the compound A, B. on dehydrohalogenation with alcoholic KOH. Ayields acetaldchyde &
propionaldehyde on ozonolysis but B yields formaldehyde & n - butyraldehyde. Identify X, Y & Z
& also A & B & give the reaction.

7. The hydrocarbon A, adds one mole ofH, in presence ofPt catalyst to form n-hexane. When A is
oxidised rigorously with KMnO, a single carboxylic acid, containing 3 carbon atoms is isolated.
Give the structure of A & explain.

8. What will be the product in the following reaction

NO,

(i) D +
H
JC Ph
--7 (ii)W +

1. NaMI12(3equiv.) NH,
(iii)cQJ" + Br , ----+) A
2. GI,[
)B

9. Conversion:
(i). C,H, --+ racemic 2, 3 dibromobutane (ii) 2 butyne --+ 2 pentyne
(iii) Ethyne--+ Acetone (iv) Methane --+ n Butane (v) Ethene --+ Propionic Acid
10. Hydrocarbon (A) C6I-I,o on treatment with H,lNi; H,lLindlar catalyst & NalNHJ fonns three ditferent
reduction products B, C & D respectively.Adoes not form any salt with ammoniacal solution but
fonns a salt (E) on heating with NaNH, in an inert solvent. Compound (E) reacts with CH)J to give
F. Compound D on oxidative ozonolysis gives n butanoic acid along with other products. Give
structure of A to F with proper reasoning.

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r II. There are.6 different alkenes A, B, C, D, E, F. Each on addition of I mole of hydrogen gives G
which is the lowest molecular weight hydrocarbon containing only one 'assyrilmetric carbon atom.
,

Norte of the above alkene give acetone as a product on ozonolysis. Give the structures of A to F.
12. An organic compound (A) contains 85.1 % bromine & reacts \vith moist AgP to yield compound
B (C,HoO,). B is oxidised to an acid (C) which evolves CO & CO, on warming with concentrated
H,SO,. Substance A on boiling with alcoholic KOH yields a gas D which on being passed through
ammoniacal Cu,Cl, solution deposits a red solid containing 84.1 % Cu. DeduceA to D.
13. Identify A to E
Alcoholic) A I. NOINH2 )
PhC;:HCl CH,CI KOH ,. CydOI"'''yl ;od;d, B
I

D+E KMno.m+ _. _
C PdlBaSO.
quinoline

14. What will be products in the following reaction?

NaNIl; ) I.NilNH2(3equi)
(a) PhC '" CH Mel A (b) PhCH = CH, ) B
2. CH)I

(c) PhC '" C - H I. HgSO•. H,O') A

2. NH10H

15. Ond of the constituent of turpentine is a-pinene having molecular form'ula CloH, •. The following
scheme give reaction. of a-pinene. Determine the structure of a-pinene & of the reaction products
AthroughE.
E(C !lHI8O,) A(CloH,.Br,)
' T H,O t Br/CCI,
I
CloH,.O(D) a-pInene Brl+H1Q ) B (C'OHI7OBr)

(i) H,SO,
(i) 0,
(ii) Me,S
1 1(ii) /:;.
I

CCC"H"Br)

16. What are A to D & a -+ ffor the following reaction:

>OJ" o

(i) c=>= --L. A-L B-£.... C>

D D OH
D""'L J"I~
I

(ii) ""'c=c( --iL. C-L D---L

MeC/
,H Me ,C / ~ D

17. What are A to K for the following reactions

(i) PhC '" CH + CH,iVlgX -+ A MClJ.CI) B UiNH,) C.
alcoholic
(ii) PhCH,CH,CH, + Br, ~ D --K-OH--) E
.J- Cold dilute KMnO,'
G ( hoI KMn04 r
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 OH

("')
n
III~~
Me Me
H

I-I,C OH bH
~
n CH,
(iv) 0 --'--+ c( bH

(v) CFJ - CH = CH, HBr ) J (vi) NIlS, I, ) K

Me Me

18. A hydrocarbon (A) of molecular weight 54 reacts with an excess ofBr, in CCI, to give a compound
(B) whose molecular weight is 593% more than that of A. However on catalytic hydrogenation with
excess of H,(A) forms C whose molecular weight is 7.4% more than that of A. A reacts with
CHJCH,Br in presence ofNaNH, to give another hydrocarbon (D) which on ozonolysis yields
diketone E. E on oxidation gives propionic acid. Give structures A to E with proper reasons.
19. A lag mixture ofisobutane & isobutene requires 20g oCBr, in CCl, for complete addition. If lag
of the mixture is catalytically hydrogenated & the entire alkane is'monobrominated in presence of
light at 127°C, which exclusive product & how much of it would be formed.
(At WI. of Bromine = 80) .
20. A& B on combustion analysis indicated C = 88.82%, H = 11.18%. Both decolourises Br, solution.
A gives a precipitate with ammoniacal AgNOJ solution. A oxidiscs to CO, & propionic acid.
Compound B does not give a ppt. with ammoniacal AgNO] & oxidises to CO, & oxalic acid. Give
structures of A & B. .
21. An organic compound A (C6H 10) on reduction first gives B(C)-I,,) & tinally C(C)-II4)' A on
ozonolysis gives two aldehydes D(C,H,O) & E(C,H,O,). Oxidation ofB with acidified KMnO,
gives the acid F(C,HP,). Determine the structures of the compounds A to F with proper reasoning.
22. Dehydrobromination of compounds A B yield the same alkene C. Alkene C can regenerate A & B
by addition ofHBr in presence or absence of peroxide respectively. Hydrolysis of A & B gives
isomeric products 0 & E respectively. I, I diphenyl ethane is obtained on reaction ofC with
benzene in presence ofH+. Give the structures oCA to E with proper reasons.
23. Identifyn,A&B
CH, = CH - CI-I = CI-I - CI-I = CI-I - (CH,),C '" C - (CI-I')6 - C '" C - CI-IJ
.j. n moles ofH,/Ni
A ('''.') mol" of H, ) B ( cod P +HI CHJ(CI-I,).-CI-I,Br
Nt

24. The following cyclisation has been observed in the oxymercuration & demercuration of this
unsaturated alcohol. Propose a mechanism for this reaction.

(f" I. Hg(OACh
2. NaBH4
)

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\

25. Propose structures for intermediates & products A to K

I bromo butane -~~--..

Mg, ether D I. CH,(CH,), -CHO
2. H.,O' I
• E

IKOH, H,O H,SO, . r:,

!
A

I
13
Na
Etl3r C
npr CHO
+ tibu CHO
~~c,sl\~F

Br,

G
fused KOH

°II 1
1'l" 1'l\-\, H
followed by NaNH,
'
NNH \~
K. (i) CH,-C-Et
(ii) H.,O+
J• a 'I-nonyn~ ,1.'"
1 __ -1
HBr

26. An alkene (A) yields acetone & an aldehyde on ozonolysis. The aldehyde is easily oxidised to an
acid (B) which on treatment with Br2 in presence ofP yields a compounds C. C on hydrolysis gives
a hydroxy acid D. D cim also be obtained from acetone by the reaction of HCN followed by
hydrolysis. Identify A, 13,C & D & give the reactions.
27. Identify the following (A to D).

D
optically inactive
+ >C = ° + CI-l,CO,H
Cf,H1oO.

CH Lindlar's C H
'13 " . Catalyst A u ll
I KMnO,(hot)

Li/EtNH,
• 4 ethyl 2,4 dimethyl
2, 5 heptadiene
optically
active lo,lzn
C",H'(lO)
optically active
+ >C = ° + CH,CO,H
C

i
28. An alkyne (A) of molecular formula C,H'2 produces 13& C on reaction with Na/Liq. NH) & H/Pd
.(Lindlar's Catalyst)). D(isomer of B) gives acetone as one of the products on ozonolysis & on
electrophilic addition with W gives E. E on ozonolysis gives 2, 7 octanedione. Identify A to E.

29. Conversion

Me2C=CH- CH,CH,CMe =CHCHO+Hp. ~

Citral

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 Explain with mechanism.

30. Write the structural fon11ulaoflimonene from the following obscrvation:

(a) Limonene when treated with excess H, & Pt catalyst, the product formed is I isopropyl' 4 methyl
cyclohexane
(b) When it is treated with OJ & then 2n/l-l,0 the products of the reaction are HCHO & following
o o
I

compound

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-

Explain the non fonnation of cyclic product in (ii)

Q.19 Carry out the following transfonnatiOli in not more than three steps. lIlT 19991

Q.20 CH2=CH- is more basic than HC",C- lIlT 2000J

Q.2l What would be the majorproquct in each of the following reactions? lIlT 2000]

CH]
I
CH] -?-CH2Br C,H,OH /'...... H
(i) .. " CI-] 2 )
6 (11) ] Lindl.r'sCat.iys! .
~
CH]

Q.22 On reaction with 4N alcoholic KOH at 175 °C I-pentyne is slowly converted into equilibrium mixture
of 1.3% l-pentyne (A), 95.2% 2-pentyne (B) and 3.5% 1,2-pentadiene (C). Give the suitable
mechansism offonnation of A, B and C with all intennediates. [lIT 2001]

Q.23 Identiry X, Y and Z in the following synthetic scheme and write their structures. Is the compound Z
optically active? Justify your answer. 11IT2002]
CI-LCH C",C-H (i)N.NH,) X 1,1, /Pd-B.SO, ) Y .lk.lincKMnO,) Z
,
2 (ii)CH,CH,Br

Q.24 A biologically active compound, Bombykol (CI6H]OO) is obtained fi'Oma natural source. The structure
of the compound is detennined by the following reactions.
(a) On hydrogenation, Bombykol gives a compound A, CI6H]40, which reacts with acetic anhydride to
give an ester.
(b) Bombykol also reacts with acetic anhydride to give another ester, which on oxidative ozonolysis
(OiHP2) gives a mixture of butanoic acid, oxalic acid and 1O-acetoxy decanoic acid.
Detennine the number of double bonds in Bombykol. Write the structures of compowldAand Bombykol.
How many geometrical isomers are possible for Bombykol? lIlT 2002J

Q.25 If after complete ozonolysis of one mole of monomer of natural polymer gives two moles of CH20
CH]
I .
andone mole of ° = C - CH = 0. Identify tllemonomer and draw the all-cis structure of natural polymer.
lIlT 2005J
X°J-l
Q.26 U W.6 ) X Ii) oJ
(ii) ZI1/Cl,COOH
) Y.

Identify X and Y. IIIT2005J

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 ANSWER KEY
Exercise I
Q.l B Q.2 C Q.3 D Q.4 A Q.5 A
Q.6 A Q.7 C Q.8 B Q.9 B Q.10 A
Q.ll D Q.12 A Q.13 B Q.14 B Q.15 A
Q.16 A Q.17 D Q.18 B Q.19 B Q.20 A
Q.21 B Q.22 B Q.23 B Q.24 A Q.25 C
Q.26 B Q.27 A Q.28 A Q.29 A Q.30 C
Q.31 C Q.32 C Q.33 C Q.34 C Q.35 C
Q.36 D Q.37 A

Exercise 3(A)
Q.I 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.I0 D Q.ll C Q.J2 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.2! D Q.22 A

Exercise 3(8)
Br
13r
@-CH-Cf-I) ulc.KOIl )@ .
CH=CH-CH, ~
CH-CHrCH)
CH 3 - C = CH - CH 3
I
CH3
2
heat
IlIlr )
@
H Me Me

3
I H+Br + Br+H
CH3 -CH2 -C -CH = CH2 4 5
Brll'l HIBr
I
CH3 Me Me
(C6H12 )

CH2 CH2
II II
6 (E) CH3 -C - CH

o
10 (A)(I) (D) 0 o
11 (A) CH3-CH2-CH=CH-CH2-CH3 (D) CH3CH2COOK
16 I -7 ozonolysis; 2 -7 LiAIH4; 3 -7 H2S04
17 (4) -7 HO-CI ; (5) -7 CH3MgCl ; (6) -7 H20/W

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19 (I) NaNHz, (2) Me-J, (3) HgS04 dil HiS04 20 higher electronegati vity of sp carbon
CH}
I
21 (i) CH} -C-CHz -CH}
I
O-C2H6
Et
Et El HiOH
23 (X) ~ Et-C",C-Et (Y) ~ H>C=C<I'I (Z) ~ H-+OH Z is meso so optically inactive.

24, Bombykol :- HO-C-C-C-C-C-C-C-C-C-C=C-C=C-C!..C-C

(A) :- HO-fCH37-tsCH34 geometrical isomers are possible
CH}
I CH)"., ......-H
25 (a) CH2 = C-CI-I=.CH2 (b) (CH ......-C=C"CH T
2 2 n

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'I

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