& REATONMECHANISM

REACIVE INTERMEDIATE
42 Years
Questions
GATE Previous

reaction
is GATE 20
he majorproducts fomed in thefollowing
Me
Me
:CHsinglet)

Me
Me
(b)
(a) H M
Me CH CHs

(d)
(c) 50 50 mixture ofabove two compounds
withHCls GATE
camphene 2000
The majorproducts formed upen heating

(Camphene)

H
b) La CI
C
in the Sy reactionis IGATE2002
3 Among the bromides
reactivity
givenbelow,theorderoftheir
-Ill

1> I>I (I1l>1>l (d)11>1>IIl

(a) ll>
Il>1
The major product fomed
(b)
in
with
the reaction
the presence ofa catalyic
benzoicacid isobutylenein
amount of

GATE 2002
acidis:
sulfuric

) (b)
OH

(d)

base

Among the followingcompounds, theone that undergoes deprotonation most readily

in the
o
presence
2003
to forma carbanionis GATE
O

(a) (b) (c) (d)

MeO OMe MeO

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 REACTIVE INTERMEDIATE& REACTIONMECHANISM 43)
6. the saponifactionofM and N shown below,the correct
Regarding statement isthat GATE 2003

COOCHs

CoOC2Hs

M N

(a)M reactsfasterthan N stateisless crowded forM than forN.

because thetransition

(b) M reactsslowerthan N because thetransitionstateismore crowded for M than forN.

()Nand M intermediatein both cases.

oftetrahedral
reactat the same ratebecauseofformation

(d)N reactsslowerthan M because ofits thermodynamics stability.

greater
The enolate ionthatreacts
with3-buiten-2-one
toform (Y)is: GATE 2004]

(a) (b) (d)

8, The majorproduct P formedin

thegiven IGATE 2005]

NaOEt. EOH
OTS

H
Ph CH3 H3C

(a) (b)
HC H

HaC Ph
Ph
CH3
() H (HC CH3
HO
ofthefollowingcyelic
towards acidcatalyzedhydrolysis
The orderofreactivity acetalsis: IGATE 2005}

NO NO2
No -NO2

(a) Z>Y >X (b) X>Y >Z (c) X>Z>Y (d)z>X>Y

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 REACTIONMECHANSM
gives.
REACTIVEINTERMEDIATE& and NaHCCCO,
I, GATE.2M
X with
acid
carboxylic
10. lodo-lactonization
of Y-unsaturated
OH

(d) FO

(a)
(c)
IO
IGATE26
is:
11 The major product P ofthefollowingreaction

B P
dark

HC CH
CH3
B CH3 HC Br

(a)
H3C
B (b)
CH3
(C)Br CH (d)
Br Br

Br
GATE 2005

12. The major product P ofthefollowingreactionis

NH2
CoOEt OH
Me
P

OEt

cOOEt
COOEt

OEt
(b)
FHN
(a) Me
HaN Me HO

COOEt
F- COOEt

FHN
(c) (d)F F
N

Me Me
OH
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 REACTIVEINTERMEDIATE &REACTIONMECHANISM 45
13 Major compound Q obtainedon rcactionofP withNaH in DMF is: GATE 2005|

COOEt COOEt

(a)F N (b)F
OEt

Me Me OH

cOOEt coOEt

14.
(c) F

Me
the majorproduc
Identify
O

Pinthe
following
reaction.
(d) F

e OEt

[GATE 2006|

O
+Cl H aq. NaOH

O
(a) (b) (c
O
15. On heatingwithdilute acid,nephthalen-I
sulfuric acidgivespremominantly
sulfonic IGATE 2006
(a) naphthalene (b)naphthalene-2-sulfonicacid
(c) 1-naphthol (d)2-naphthol
16. Predict
the major reaction
P in the following IGATE 20061

OH Me
Me
HNO
P
Me
NH2

Me

(
(a)
Me
Me

Me
(b)
Me
Me

Me OH Me
OH
Me

(c) Me (d) CH2

OH Me

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 MECHANISM
&REACTION
REACTIVE INTERMEDIATE GATE
46 following
reacto:
2006

P in the
17. the majorproduct
dentily Oli
OLi
(i)
CH,CH/THF P

OEt (i) H,O*

OCHCH3

(b)
OEt
(a)H3CH2CC OEt

OCH2CH3

OEt (d) OEt

(c)
GATE 2006
CH2CH3
reaction:
P in the following
18. the major product
ldentify
SiMe3
CalhCOCl
TICly

COCH COCH
cOCH
cOCHs
(d)
(b)Me S
MegSi
(a)
IGATE 206

LinkedAnswer Q.19 and Q,20

the major product P in the followingreaction
19 ldentify

CHCH(C)coCI P

Et3N/0-5°C

(d) CH
(b) chs C

CI CI
CH3
[X],
theintemediate a
respectivel.
20. In reaction,
witting
thefollowing thestructureofthemajorproductPand

ArCHO+ Ph,P = CH-CH,CH, BengeneSIX1PP

Freeot
10organicsalts

Ph3 Do.
Ar
A.
Ar H

(a) (b)

PPh3
PPh3
Ar H
Af
(c) (d)
H

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 REACTIVE INTERMEDIATE& REACTION MECHANISM

21. (a)-(d)givenin List

Match the reactionsofsome p-substitutedbenzene derivatives Iwiththe Hammett'sp-
values)-(iv)
II
in List and identifythe correct
match. IGATE 2006]
List-I List I1
ArCH,-CI
(a) 70 nArCH,-OH+HCI
C ) +8.50

H.O
(b)ArCH,-CO,H 25 C
ArCH,-CO0 +H (it)
+

(c)Ar-ClMON 50" C Ar-OMe + CI +0.49

(ii)
(d)
Ar-CO,H 25 C Ar-CO0 +H -1.88
(iv)
d-ii
d-iii (c) a-i,b-ii.c-iv, (d)a-iv,b-iii, d-ii
c-i,
(a) a-i,b-iv,c-iii,
d-ii (b) a-iv,b-i.c-ii.

22. The majorproduct obtainedupon treatmentofcompound X withH,SO,at 80°C is: IGATE 2007

HO
(X)

(a) (b) (d
23 In
thefollowingcompound. the
hydroxygoup thatismost readilymethylatedwithCH,N,is:|GATE
2008

P
HO OH
HO

HO

p
(a) (b) (c)r (d)s
IGATE2009
24 Inthereaction,
excess

anhy drous AICl

Me
the major product X is:

(a) (b)Me
Me

Me

d)
Me CoOH

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 MECHANISM
REACTION

48 REACTIVEINTERMEDIATE&
GATE 2009
PhP-CHCOOE X]1
Inthe reaction, CHO
25. Ph
the majorproduct X is: EtOoH
H CoOEt (b) CHO
Ph
(a) CHO
Ph

COOEt (d)ph COOEt

()Ph in the reaction
GATE 2009

conformation)
on the preferred
X
26. The majorproduct (based
OTs
H

KH X
OH

OTs

(d
(C)
(b)
(a) OH

CHs

NNHSO NaOMe
[X IGATE2010
180°C
27. Inthereaction,

the majorproduct[X]is
CH3
CH3 CH3

(a)
(b) (C) (d)

2010
28. Inthereaction,
HNO2X] IGATE
OH
the major product [X] is

CHO
(a) (c) (d)
OH

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 REACTIVE INTERMEDIATE& REACTION MECHANISM
49
29. ldentifythe most probable product in the given reaction IGATE 2012

O,/benzoyl -
peroxide Product

OOH
OOH
0OH
(a) (c) (d
OOH

30. Show below isa Hammett plot

obtained forthe reaction IGATE2012

P4.4

O
2.55
HO
Ar Ar OH

Thechange inslope oftheplot that

indicates

linearfreeenergy relationship
(a) The reactiondoes not follow

(b) electrons fromthe transition

arebeingwithdrawn statein the mechanism

are being donated tothe transition

(c) electrons statein the mechanism

(d) ischanging
the mechanism ofthe reaction

31. Inthe reaction, GATE 2012

H
KOH-EtOH Product

the product formed is

O
(a) (b) () (d)

CHO

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 REACTIONMECHANISM
INTERMEDIATE&

50 REACTIVE

and Q.33 givebelow.

theenergyprofile
GATE

Common Date forQ.32 from

halides
Consider the El actionoftert-amyl

Kcactuon cO0rOLa

Elreaction
M N
R-

halides(R-S)as
the alkyl SIS2ani
Intheabove reaction,X=CI,BrorL Based onthegraph,identify
32 R-Brand $3 = R-CI
(a)SI =R-CI.S2=R-Br and S3=R-I
(bSl=R-,S2 =

$2= R-Cland S3 = R-Br

(d-SIR-1.
(c)S1 =R-CL,S2= R-Iand $3 =R-Br
to P
33 product
Identify P and its relative
yicld

(a)
PisM product
and isthemajor
(b P isNandisthe minorproduct
(c)P isN andisthe majorproduct d) M andistheminor P is product.
GATE
34 In
thecyclization givenbelow,
reaction product formedis
themost probable
201

NaH
OH Product
HO
HO
HO
(a) HO (b) HO
(c)

35. The major product formed in thereaction

givenbelow is GATEW

NH2
NaN0,,aq.H
0-5°C

C NO2

NO2
(b)
OH

OH
(C)
(d)

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 REACTIVEINTERMEDIATE & REACTION MECHANISM

36 The major product formed in the following

reactionis IGATE 2014
H
Ph H202
Ph heat

SePh

Ph Ph
(a)ph (b) C) Ph (d)
Ph h Ph Ph

37 The major products X and Y formed reactionsequence are

in the following GATE 2014

NO2
EtONa. EtOH
X
OTiCl3
Y

(a)X= Y
NO2

=
(b)X

NO2

NO2

OH

Y
(c)X=

NO2 NH2

OH OH

(d) X= Y

38. orderofthesolvolysis
The correct chloridesin aceticacid is
forthe following IGATE 2014
CI CI CI

(1) (11) (I)

(a) I1>1>Il (b) I1>I1>I (c) I11>1>II

Near 1IT,
Hauz
(d)1> Ill>II
Delhi-16
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 REACTIONMECHANISM
is
reaction
REACTIVE INTERMEDIATE&
S2 ofp-haonitrobenzenes
ofreactivity
inthe following

NO2
GATE

39. Corectorder
NO2
NaOMc
MeO

CI
(X=F.
Br. ) obenzene>p-bromonitrob
enzene
p-fluoronitrobenzene:
p-iodonitrobenzene>
(a) p-chloronitrobenz p-1odonitrobe
p-bromonitrobenzene> enzene
p-chloronitrobenzene>
(6) p-fluoronitrobenzene> p-fluoronitroho.
p-chloronitrobenzene>
p-bromonitrobenzene>
(C)p-iodonitrobenzene> nitrobenzene
p-fluoronitrobenzene
> p-iodonitrobenzenep-chloronitrohe
(a) p-bromonitrobenzene>
X manly
IGATE2M
activecompound gives,
40. ofthe optically
Solvolysis

MeO Me
AcOK
AcOH
OTS

X Me

MeO Me
MeO
Me

OAC
OAC (b)
(a) Me
Me
active)
(optically
active)
(optically

MeO
MeO Me
Me

OAC OAC
(c) (d)
Me Me
racemic racemmcC
(opticallyinactive) e)
inactiv
(optically

The major product formed in theföllowingreaction IGATE 201

41 is
Me
Ac0, NaOAc
afdre

(
Ph H0

guphuut
Q
ad Me
Me Me Me
(a) (b)
(d)
OH

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 REACTIVE INTERMEDIATE & REACTION MECHANISM
53
42. The major product formed in the following
reaction,
is IGATE 2016]

PhBr(I
equiv.)
Cat.Pd(PPh3)4

KOAc, DMF
CH3

Ph
Ph Ph
(a) (b)
Ph (c (d)
cH3 O CH3 CH3
O CH3

43 The major products X and Y formed formed in the followingsyntheticscheme are

in the following

cat.Ht
H
ben zene (solvent)

Gii)
(X)(H3C)2SCH2
IGATE 2016]

(ii)
H H0
(iv)aq.NaOH, heat

()X- y

o
b)X = Y

(c)X= Y
C(d)x=
44. The major product Obtained in the following
reactionis IGATE 2016}
(i)
LiNH2 (2equiv.)liq.
NH3
H-CEC-CH2OH
i)
(i)
CoHsBr(l cquiv.)

H,0
(a)HaCHC-c=c-CHOH (b) H-C=C-CHOCH2CH3
c)HCH2C-c=C-CH;NH2 (d) H-CC-CH2NH-CH2CH

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 MECHANISM
& REACTION
REACTIVE INTERMEDIATE
54 Is
reaction, GATW
in the following
45 The major products fomed

i)CHsl warm
N(C2H5/2i)NatiCOy/MeOH,

OCHa

NC Hs2
HC NCaHs)2 (b)
(a)

CH3
CH2 (d)
c) CaHs

N reactionsequence
in the following are IGATE201
46. The major productsMand

CH3
Hal LIPPh2
CH + Lil
(M)- (N) PPh2
H3CO CH3

Ou HC CHa

M= HsC N=
(a) H3CO CH3 HaCO-
PPh2

OG H3C

M HoCi N
(b) H3CO CH3 HaCO
PPh2

OuH HgC CH3

(c) wM= HsCl N=
H3CO
PPh2
CH H3CO

OLi
H3C H
HsCl
M
(d) N=
HgCO CH3
PPh H3CO
CH3
47. Among the
following
decahydroquinoline
toluenesulfonates
(Ts),
the one thatyields9-methyla
Senal as a majorproduct upon aqueous is
2011
2017
solvolysis
/GATE
TsOH TsO
TsO
TsOH
(a)
N (b)
() N (d)
CH3
H HCHs
CHs
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 REACTIVE INTERMEDIATE &REACTION MECHANISM
55)
48. The product obtlainedin the following reactionis
solvolysis IGATE 2017

NaOAc/AcOH
OAc
CH3 moC
Enantiomerically
purecompound

(a) a racemic mixtureoftrans1,2-diacetoxycyclohexane

(b) enantiomerically
pure trans 1,2-diacetoxycyclohexane

) racemiccis 1,2-diacetoxycyclohexane

(d) a mixture ofcisand trans 1,2-diacetoxycyclohexane

49 The major product obtained in the followingreactionis GATE 2017

MeO OMe 2.2-Diinethoxypropane

(catp-1ohuenesulfonic
acid)

OH OH

MeO
O

OMe
OO
(a) o (b) (C)
MeOOC

OH OH
OH
50. The majorproductformed in the following
reaction
sequence is IGATE 2018]

( LDA.-78C
i) PhSeCI

(ii)
HO

SePh PhSe

(a) (b (c) (d)

51. The major productformed inthe followingreactionsequence is

6HOC SO2Ns
(ii)
Rha(OAC)4
-NH CO2Bn
O
=0
-N (b)
(a)
CO2Bn
CO2Bn

=0
0
(c) -NH (d) o
0 Na COBn
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 MECHANISM

56 REACTIVEINTERMEDIATE&REACTION
the followi
sequence
reaction
is
GATE 2
52. The majorproduct formed in 55
()mCPBA, NaHCO
MeO NaOH, H20
(i)
I
(ii)KI,NalHCO;.
H0

MeO

(b)
OMe
(a) HOl.A

OH

MeO

(d) Me0
(c) HOY HO

reactionsequence is GATE 201

The major product formed in the following
53.

Fso
i
(ii)
KO'Bu
Raney-Ni,

(a) (b
o

(c) o (d)

O
54. The major product formed in the following
reaction
sequence is GATE20

EtAICI
benzene
Chc 5 °C

Ph o Ph
(b)
()CiC Ph Ciyc Ph (d)
(d) o
OH
OH Clc
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 REACTIVEINTERMEDIATE& REACTION MECHANISM
57)
55. The major product formed in the followingreaction
sequence is IGATE 2019

HOTs
AcOH

H OAc AcO
AcO OAc
(a) (b) (c)

56. reactions,the major product (P)and (Q) are

Inthe following IGATE 2019)

OR

Q
PhCOaH PhcOH
benzene,0 °C benzene, 0 °C
R=H R= COEt

OCOEt OH

(a) P=

OCOEt OH

(b) P =
o

OCOEt OH

(c) P Q

OCOEt OH

(d) P= a

57. The major product formed in the followingreaction

sequence is IGATE 2019

O NaOEt
+HCHO
OEt EtOH, A
HC (2 equiv.)

6)HC C)
HC
(aHC COOEt COOEt
COOEt COOEt

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 MECHANISM
REACTION

58 ne
58
REACTIVE
INTERMEDIATE&
sequence
reaction
formed in thefollowing
is
GATE 2
major product

1.CH MgC
H
2. HCI

CI

CH3 (d)
CH
(a) cHs

ANSWER KEY
6. (c)
3.
4(b) 5. (a) 7.(e)
1.(a) 2. (a) 13.(d)
11.(d) 12.(d) 14.(a
8. (d) 9.(a) 10.(d)
18.(c) 19.(b) 20.(a) 21.(0
15.( 16.
(a) 17.(a)
24. (d) 25. () 26.(a) 27.() 28.(b)
22.() 23.(b)
33.(d) 34.(C)
32.(b) 35.(d)
29. (c) 30. (d) 31.(b)
40. (c) 41.(d) 42.(
38. (c) 39.(b)
36. (c) 37.(a)
45.(c) 46. (a) 47.(c) 48.(a) 49.(b)
43.(b) 44 (a)
52.(a) 53.(a) 54. (b) 55.(b) 56.(b)
50.(b) 51.(a)
57.(d) 58.(d)

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