•••••• ••

••
~ Phenols
•
l
(25\.
'
'••
••
•••••••• •
♦ and Ethers
4. What 1s ·x· in the given reaction?
CH20H 21o•c
f1. preparation and Properties of l
CH20H
+ oxalic acid-- - x
maJor product
Alcohols \f<eh. 25, 2021 II
'fheillajorproduct formed in the following reaction is : CHO
!Aug. 31. 2021 (l)l (a) tHO
CH3 CH-OH CH 20H
I (c) II (d) II
C CH CH cone. H2S04 CH 2 CHO
CH, - - - 3 a few drops ➔ Major product
5. What is the final product (major) 'Nin the given reaction?
I I \hhruan 2-1, 2021 ll,I
CH 3 OH

(a) CH-C==CH~I\C1¾
I 3

~ 'A'
(b}

M'
{major product)

H3C CH3
(c) CH,,
C=CH-CH3
CH/"....-

~
To synthesise 1.0 mole of 2-methylpropan-2-ol from
Ethylethanoate _ _ _ equivalents of CH 3MgBr
reagent will be required. (Integer value)
''
1
I. ?.I\, 2021 (1)1
Ceric ammonium nitrate and CHCl/alc. KOH are used for
e identification of functional groups present in _ _
and_ respectively. lhb. 26, 2021 (11)1
(a) alcohol, phenol (b) amine, phenol
(c) amine, alcohol (d) alcohol, amine
 !liJl!l!l''Rtomajf1r product of the fi,llm, 111!,l rc.,d11111 is.
j~, p. o-:, 20211 (11)1
(hi A
I !~II <»I
IIO~(IUII, If,( OIi C 11,
Jf ,SOJ
➔
u,,
()
J
[ J
Clo 60
C IU 11 1 l'll ,Clf,
(C)
~OH
<•l <hl lliC CH 1
. OH
HF\ r-\j J--OH

(cl o:: (d) &O

When neopentyl alcohol is heated with an acid, it slowly
to.
(d)
H3C
n
HO CH3
r
Heating of2-chloro-l-phenylbutane v.,1th EtOK EtOH
X as the major product. Reaction of X v.,ith Hg (QA:;
H,0; : ~Y as the major product. y
converted into an 85 : 15 mixture of alkenes A and B.
respectively. \Vhat are these alkenes? fSep. 04. 2020 (])I
H3C fH H3C\___/CH 3 •
(a) I I \pril 12, 2019 I
2
OH
(a) ~ and r OH
H3C CH 2
CH3
(b) I
Ph~
H3C\ FH3 H3C, j OH
(b) F' and lf (c) I .
H3C CH2
Ph~
CH YCH3 CH3 CH2 (d)p~
3 \__//
(c) and ,· OH
CH2 CH3 11. CH 3 CH 2 - C - CH 3 cannot be prepared by:
H3 C')=/CH 3 H3C~CH 2 Ph
(d) d f (a) CH3CH2COCH3 + PhMgX (Jan. 12.2019(1
an
H3C H3C (b) PhCOCH2CH3 +CH3MgX
8. The number of chiral centres present in [BJ is _ __ (c) PhCOCH3 +CH3CH2MgX
fSep. 04. 2020 (1)1 (d) HCHO+ PhCH(CH,)CH,Mg,X
0 ~ - -

0-
(i) C2H5MgBr

O
CH-C=N - - - ~ [A] CH2 -C -OCH 3
f (ii) H30 +
CH3 12. NaBH,
---"-.._X
MeOH
(i) CH 3MgBr
0 ~
9.
[BJ
(ii)Hp
The major product of the following reaction is:
!Jan. 08, 2020 (1)1
(a) u
~ C H2 -C-H
!Jan. 10. 20\Q I

OH

(b) V
~CH,CH,OH
. 4

(a)
(c)
& ~
CH 2CH.,OH
•

(d) &H, i C-OCH3

 c-160

e,z•@m_____
PNparation and Pn,perttel Of
Phenols
~---='

(c)u
J:
()JI
(d)

&
I
>Ji

z The orrcc1 l f :\ nd J4 ft rmcd tn lhC' folio\\ 1111 Off

f\u " OZl(ll)J
() tl

AOA ~f'~/•,~(J,
C f H fl\ B A fJ
IO cq (MaJur ProduL1l
consider the above rcact1011, ,ind choose the c rrec.•
slatcmen t • J 2"' f
0 (al The rcac11on 1s not possible m ac1d1c medium
(b) Both compounds A and B arc formed equally
(c) Compound A will be th e maJor product
A B: CH 3 (d) Compound B will be the maJor product
32. Reaction of Grignard reagent. C2H5MgBr \\-1th CgH O
followed by hydrolysis gives compound "A" which reacts
NH2 1\TH2 instantly with Lucas reagent to give compound B
0 0 C H CJ. f\lnrct ,., ~ it f

k~~:
10 13

~
ACH. OACH
l

£CH
O" 011
(a) -"- (b) J
(b) A : B: ~ J

Cl
NHYCH3
~Cl YCH,
0
0
0
(c) "CH, (d)
OACH
II L'l, • .Z6, 2021 (11)1

(c) A:
~o 3
33. Identify A in the given reaction.
OH
B:~

NH 2 yY
~I SOCl2
A (major product)

~B~
HO CHpH
(d) A:
OH Cl

NHYH3

0
l . Which one of the following phenols does not give colour
(a) c;¢ QQ (b)

OH CH2Cl OH CH,OH
when condensed with phthalic anhydride in presence of
Cl OH

c;¢ c;¢
cone. Hz$<),? jAug. 26, 2021 (11)1

(c) (J)

(a) V
~OH
(b) Cl Clf /'1 Cl CH.Cl
 c~161
"'" pi,enols 11 nd_Eth_e_rs
1f1,~ 111 ----
_,.,,.'...- f 11..,wl in rhh110t,11111 "hen It l·11t1·d with • order of
unclll in increasing
0 r • •
0111t11lfl 11 uiH's n,m,h111111! I' ,ts 11 111111111 pwd111 l
,H. ,\r11111gc the lt,llowmg l01t1po cnol p -cthoxyphenol
\ ~ NII() e . , . I • c c)If ho11d length ' rncthnnol, PI1 •,. ms
2020 (I >I
, qii ('(lll~ ' (l<'fl'C'f ,wgi• ,,1 1'.11h,u1 111 I 1s ( to l 11 1 111
o,e 11111~~ ~,. r)(,\tlimir mus~ t' 12: 11 I: 0 lh) (u) mcthnnol . /I cl IioKyp,I cr111I ;' phenol
henol
11 1
~1111lq;c I'\ "• I' Or, II 1(1111 ( ;:' , .cthoxyp
{h) phenol · met IJut1o 1 thrsnol
"" . 11,ltll, I,r I tc, 11f b1ultllg po111t:- Iii • t I\C 1·o II ow111g (c) rhcnol · p -ct Imxyp hcnol < rnc henol
""'l' 1n.rc, . l'-••1 1, ti ll ( IJI (ti) methanol · phenol .., fl •Cth oxyph n m•crcsol 111 rea cted
, ,, i111d:- ,~ .
n11"'1 .w Whnt will be the maJor Product . .w cCH Br) in presence of
()II OIi
,-(!
()JI 011 with propargyl bromide (HC C i,
:,ril 12 20 I'> ( II H

K ,C ~ ~ 1"'1(011 #
~tt
II
(a) y Iii (b) ~ -

~ 0
NIL OCH 3
Ill IV

(Jl
1,<..111 < I\' .....~ II
I < II < Ill
(b) I <- IV . . _ Ill <... ll
(d) III <.. I.. ._ II <... IV
(c) ~ "'
(d)
c~
0
(,•) JV'- ' reaction
• .' CH~ ·ng reaction is :
ts . th.1: following
('on~1dcr ,. . .,. I~· • - 020 (11)1 ThemaJorproductofthefol 1owi IJan.11,2019(1)1
40
)J 0@(1 ii)

Cb .._ (i) HBr

(ii) ale.KOH
~

cp f
a
("hrom1c • 'P'
anb)dn; t 'P' gives positive eerie amrnonmm nitrate test. (a) (b)
Th: P: uc , Of the presence of which of these -OH
This 1s because
grou~~s)?
(a) ('.t)only
(c) (1v) only
,. Themajorproductofthe o o
j1',l•p. 113
(b) (iii) and (iv)
(d) (ii)and(iv)
fi 11 wing reaction is :
. i.
l OI I I

1120(11)1
(c)
Cp (d) 0
)-II
. produc t of the following reaction is :
41. The maJor

cone. HNO, + cone.

H,S04
Br 2 (excess)
(Jan.11. 201() (1)1

OH

[a) u,c~
0 2N N02
(b)
H
3
C9'
' OIN 02

::::-.... N0 1
(a)
B'qBr~I
~ (b)
~r
OH

OH
Br SOJH
H3C*9'
N 02 I OH
:::::-.... N0 B r
2
HI
NO?
(c) (d)
Br Br
Br
-eat1,htiH3iMD . . 52. Which one of the followrr.g ~ , a: 7"_,,.
11
~~
6

fbe major product of the follo\\1ng reaction 1s: ~ o- "

Jq, (Online .\pril 8. 201il mC61efi"ec1r.emsr~.gtheJi°~#v 0:
o ',, 1 2 14
~H
(a) -0-t tbJ -OGl-½
(c) -COCH~ (dJ -~OH
~OH 53. Which one of tte folkr.;..-mg ~ d s WI, r.!lt be sc.-~
in sodium bi..:arbouate? On ne \pn I ~ 2 ..
(a) 2, .!. 6- T:ir,iw~her,oi (o) ~ ~~ •
(a) ~ C H, (c) o- Nitropr,enol (d) :senze--~ ~~.:.m: - ~_:
54. Arranze- the follcrwfa!:!
- corr.;xi,;n.ds tr. O!d!-:' ofdta~
2 pg

~)co
~OH
aciditf: OH

¢·¢(; Cl
(I)
CH
llJ
3
~0-
•••
OCH,
I CTV)
(c)~
(a) u::.-r:.,.,r,,,.m fo >!:.,.,.::,.,..!"':
c) T II n· (d ' •.
~· ,,, TTY ~
ID ,,;, •,,, ,,, •. ....., ,.,.. .r ,,, ,._
55. What is the strJ.cture ofilie rr.a_j(h p;,:;c_:t ,;.~ p~.. ~ ts
OCH3 (

oc: OCH3 treated with bromi;:e water? onr ne i\pnl .!2. 2 1'
(d)
#
50. Sodi~ ph_enoxide when he~ted with CO 2 under pressure
at 125 C )1elds a product which on acetylation produces C
(aJ B,qa, 0H
I

(OJ

Br

The major product C would be

Br
56. Toe reaction of p;.enol v.iili be--..zoyl chloride to gPoe p:.!tlyi

(a)
OCOCH3

6--COOH (b)
lrcOCH,
y
benzoate is known as :
(a) Clai:;e1ireac-c.ion
Online April 2'· 2 13
(bJ Scr,roen-Ba:/::na:J:! rea::noo
(c) ~-T~rea:nrn (d) Ganerrn.an-Koc~ rea...'"tioo
57. The major product in die followinz rea::non is :
C0CH3
CH,OH -
I -

(cl
OH

6--coocH, (d)
O-
0COCH3

COOH
Q OH
-HO
Hea: !Online \pril 2.:., 2 1'\

CH-OH CH-OH
5t. The following reaction

~
6 ◊Cl
OH (a) (b
Anhyd.
OH
V
+HCl+HCN ZnC1 2 OH Cl
CHO
CH-Cl CH-Cl
is known as: (Online \pril 11. 20141
(a) Perkin reaction
(b) Gatterman-Koch Formylation
(c) Kolbe's reaction
(d) Gattermann reaction
(c,
Q Cl
(d A
~
OH
 1~ •:2ru•

ln l Rc.:1111C'1 I 1t~11.11rn a :,11111111

(b ) l lt11,111 rr.ll t11H1
(~e1,nd of Ethers
propertl••

, . , two ,i tat cm cn tR, one Jfi lt1bc1t,c1

11111111.uo's ll'.ll llllll
(l) ( ' (,, c'.·1vc11 l,c 1ow ,ir e
(J) llcll • \11lh u1,I /d1nsk y 1c11dion
u 111111 (M :111d the other ii, J1.1hcll ed ,th It, , 'r ti,
11icrorro.~t m1cf ol nc,d ~11 mgth of the tollo\\'tlll,! l'CHllfl<>IHHh, . Synth csu, of ethyl ph enyl ether ma; L
111 1 \ lj~( ff I(Ill (\) • fK
( \ ) Phenol (B) 1, Ctl",ol : ; • I
ad11cvcd by WJlliam•,1111 i;ynthc~111.
{C) m N11rophrnol (D) I' Nrt111pltrnol tfru1,on (JI Heal lion of t,roJT1'1hcn1cri c with
I
(o) D C-,\ • B (h)B · D •/\ ' <' L.:1l1<1xidc y1cJdi, cthyl phenyl eth er.
(ll A .. B • D · C (dJC "' fi " /\ I> In the light of the ahovc ~tatcmcnt R,_ ch,x>1ie the
(1 1 Com,Hkt the following rcact10n : approprf :ilt answer from the option', gi ven bel<1W,
C' lll )II -+- H SO4 ~ Producl I \u' 27 2'121 I
2 2
Among the following, which one cannot be formed as a
(a) Both (A) and (R) arc correct ancJ (R) ici the cmr~
product under ,my conditions'! j201 I R"il
(a) Ethyknc (b) Acetylene explanat10n of(A)
(c) Diethyl ether (d) Ethylhydrogcn sulphate (b) (A) is correct but (R) is not correct
61. The major product obtained on interaction of phenol with (c) (A) is not correct but (R) j'{ correct
sodium hydroxide and carbon dioxide is 120091 (d) Both (A) and (R) arc correct hut (R) i~ N<Jf the correct
(a) sa!Jcylaldchyde (b) salicyltc acid explanation of (A)
(c) phthalic acid (d) benzo1c acid (17. The major product rBI in the following reacti<JO Ris:
l,2. Phenol, when it reacts first with concentrated sulphuric l~c p. 04, 2020 "'
acid and then with concentrated nitric acid, gives 12 1111sj CH 1
(a) 2, 4, 6-trinitrobcnzcnc (b) o-nitrophcnol I
CH CH 2 CII Cfl 2 OCH 2 CH 3
(c) p-nitrophcnol (d) nitrobenzene 1
11 2 04
6 t The structure of the compound that gives a tribromo HI
llcal
[Al aJCO h0 I ~ ~tB j
derivative on treatment with bromine water is j 21H11, j CH
I l
CH3

(a) OOH ~)¢ p13

(b) Cfl 3 Cll = C - Cf-1 )

~
CH2 C - CH2 (d) CH , CH,-CH- CH
(c) CH~
OH 68. The maJor aromatic product C in the foll .
CH3 CHpII sequence will be .
· owin g reaction

6 ~
l~cp. 02, 2020 ,1

0
VoH
(c) (d) 0
II Br
(excess),
fl A
(1)
.
KOH (A le)
+ B

OOH
(11) 11

64. + CHCI,+NaOfl--->~o Na' C

(a . e ea ove reaction islCHO

The electrophile involved in th b V-
200,, I (a) ~OHzn111,o' @CH
) tnchloromethyl anion (CCI )
{b) formyl cation
3 ~ CHO (b)
C01H
(c) phenoxide ion
(~) ~ichlorocarbene (c) ~ B r @:Br
(". P1cncacid is:
120021
~ C02H (d) 0
COOH

6
69· Ano rgamc · compound 'A' (CH

~)6
COOH con CHO
c. HI undergoes cle 9 100) when treated w•th
(aj 'C' . 'B' gives
. yellow prec.
avage . ld
. to }:e compounds 'B' and •
'-No2 tautomerizes to •D' •D' i~1tate with AgN03where as 'C'
'-OH could be ·• · gives positive 1·00 o,onn
r test 'A'
COOH
I' P 02.,121 I
(c) O,N*No,
fdJ6 '-NH 2
(a)
0 -
0
CH2 CH CH2
NQ2
 165
.. phenols and Ethers
~,,01• 015 I
.. , . 1-mcth)i cth) lcne o..·odc whco tft'.:itcd ,,,th an ex~' ol
(b)
0 0 - CH = CH - CH
3
1tBr pmducc~.
(s) ==( Br (h) Br
Br

(C) o C H,- 0 - CH a CH, CH3 ( H,

tt,Co-
Br
(J) ~
0
Br
(di -rn-rn,
~2. The major product l) f th~t't,tk)\\'11\£ re:ict1on 1,
\prll l l
o. · h • A and B with m0 1ecular formul
Atnong theAcompounds
cr·.
1-t p
1 3
, 1s avmg higher boiling
~mttheB Tha
ossible structures of A and Bare· • I , \ '• ~
k
· ( 11) le
P
(a) A"'HO OH

HO

(a)
2 ,0H I
(b)
(-

~ ~
~
'
,i

'--oH

YI
";\C
NC OH

(c) XOH I
(d)

NC l
NC I
B=HO OH

HO
(c) A=HO OH

HO

B=HO
OH

B=HO OH

OH (d)
 , , \, \h~\ '''l'" \,, \\ 1 11 \\
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