11

IIT-JAM CHEMISTRY 2023

TEST : NAMED REACTION & REARRANGEMENTS
Time 00 : 45 Hour Date : 29-09-2022
M.M. : 35
INSTRUCTION:
1. Attempt all the questions.
2. Section-A contains 10 Multiple Choice Questions (MCQ). Each question has 4 choices (a), (b),
(c) and (d), for its answer, out of which ONLY ONE is correct. From Q.1 to Q.5 carries 1 Marks
and Q.6 to Q.10 carries 2 Marks each.
3. Section-B contains 05 Multiple Select Questions(MSQ). Each question has 4 choices (a), (b),
(c) and (d) for its answer, out of which ONE or MORE than ONE is/are correct. For each correct
answer you will be awarded 2 marks.
4. Section-C contains 06 Numerical Answer Type (NAT) questions. Q.16 to Q.17 carry 1 Mark and
Q.18 to Q.21 carries 2 Marks each. The answer of each (NAT) is a real number.
5. In all sections, questions not attempted will result in zero mark. In Section–A (MCQ), wrong
answer will result in negative marks. For all 1 mark questions, 1/3 marks will be deducted for
each wrong answer. For all 2 marks questions, 2/3 marks will be deducted for each wrong
answer. In Section–B (MSQ), there is no negative and no partial marking provisions. There is
no negative marking in Section–C (NAT) as well.

PART-A
Q.1 to Q.05: Carry 1 Mark each.
1. The major product (P) formed in the following reaction
O
NaOH
Me Me (P)
EtOH
O

O O

Me
(a) (b)
Me
Me

O
Me
(c) Me (d) Me Me

2. The major product (P) formed in the following reaction is

O O
KOH
(P)
H+
HOOC COOH

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 22
O O O O
O
OH

HOOC COOH (d) OH

(a) (b) COOH (c)
COOH O O COOH
COOH O
3. The major product (P) formed in the following reaction
CHO CHO
KCN
+ (P)
EtOH, H2O
Cl

CN

O OH

(a) (b)
OH Cl O Cl

CN CN

(c) (d)
O Cl Cl

CN CN
4. The major product (P) formed in the following reaction,

O
(i) m-CPBA
(P)
(ii) LiAlH4

OH
HO OH

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

OH
H OH O OH

5. The major product (P) formed in the following reaction

CHCl3, KOH
(P)
Bu4NHSO4, H2O
N
H

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 33
Cl

Cl
(a) (b)
N N

CH2 Cl

(c) (d)
N N
H H
Cl
Q.6 to Q.10: Carry 2 Marks each.
6. The major product (P) formed in the following reaction

(i) O3, Me2S

(P)
(ii) K2CO3, MeOH/
BPSO
H

O
O
(a) (b)
BPSO BPSO
H H
O
CHO
CH3

(c) (d)
BPSO
BPSO
H
H
7. The major product (P) formed in the following reaction
O

CO2Me
(i) Br2/Et2O (2 eq.)
(P)
(ii) NaOMe/MeOH

O
CO2Me MeO2C CO2Me MeO2C CO2Me
Br CO2Me
CO2Me

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

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 44
8. The major product (P) formed in the following reaction

(i) SOCl2
(ii) NaN3/H2O
(P)
(iii) heat
(iv) H2O/H+
C
O OH

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

CH2 NH2 NH2

O

9. The major product (P) formed in the following reaction,

O

(i) NH2OH, HCl

(P)
AcONa
(ii) H+, H2O
MeO
(iii) BH3/THF
OR

H OH
NH2 N

(a) MeO (b)

MeO
OR
RO

H
N NH

(c) MeO (d) MeO

RO RO

10. The major product (P) is

CHO

(i) Ph3P, CBr4

(P)
(ii) LDA (excess)
(iii)
Cl
CHO

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 55

Br

Br
(a) (b)

Br

(c) (d)

Br

PART-B

Q.11 to Q.15: Carry 2 Marks each.

11. Select the option(s) in which correct major product formed with their reaction condition,
OH OH
Na2CO3, H2O2
(a) THF, DMF, H2O
Me
OH

O
Me Me
COOMe
COOMe
NaH, Toluene
(b)
COOMe
Me Me Me Me

Bn Bn
CN

(i) HN(Me)2, CH2O

(c) (ii) KCN, DMF
N N
H H

OH DEAD/ Ph3P O
(d)
THF
COOH
O

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 66
12. Correct statement(s) in the following is/are
(a) In Pinacol-Pinacolone rearrangement, migratory aptitude order is
NH2 COOH CH3 NO2

> > > >

(b) In Baeyer-villiger oxidation reaction, migratory aptitude order is

3º > 2º > Benzylic  Phenylic > methyl
(c) In Beckmann rearrangement migratory group are anti to hydroxyl group
(d) Carbanion intermediate formed in semipinacolone rearrangement.
13. Select the correct relationship in the following
Intermediate Product
(a) Benzoin condensation Carbanion -hydroxy ketone
(b) Cannizzaro reaction Carbanion Acid + Alcohol
(c) Curtius Nitrene Amine
(d) Simmon’s Smith Carbene Three membered cyclic product
14. Correct statement(s) in the following
(a) Carbocation can rearrange in the Pinacol-Pinacolone rearrangement
(b) Carbocation can rearrange in Friedal Craft acylation reaction
(c) In Mitsunobu reaction inversion of configuration occur
(d) In wittig reaction, formation of four membered ring transition state
15. Correct major product with appropriate condition
OPh OPh
Me Me

LDA
(a)
NNHTs

Me Me
CO2Me
Na, NH3 OH
(b) alcohol
CO2H COOH
COOEt
COOEt
NaOEt
+ EtOOC–COOEt O
Toluene, Et2O COOEt
(c) COOEt
COOEt

O COOEt
O

(d) ClCH2–COOEt
KOtBu, tBuOH

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 77
PART-C
Q.16 to Q.17: Carry 1 Mark each.
16. Carbene intermediate formed in the following reaction
(1) Reimer Tiemann reaction (2) Simmons smith reaction
(3) Wolff rearrangement (4) Wagner Meerwein rearrangement
(5) Wittig reaction (6) Corey fuchs reaction
17. Number of radical initiated reactions in the following is ____________
(1) Cannizzaro reaction (2) Clemmension reduction reaction
(3) Acyloin condensation (4) Mc-murry reaction
(5) Birch reduction (6) Perkin reaction
Q.18 to Q.21: Carry 2 Marks each.
18. Number of product(s) formed in the following reaction,
O O
TiCl3, Zn
+
H3C C2H5 Ph H
19. Number of aldol product(s) formed in the following reaction,

(i) O3, Me2S

(ii) NaOEt, H2O

CH3

20. Number of reactions/rearrangements in the following in which Isocyanate intermediate formed ________
(1) Hofmann rearrangement (2) Curtius rearrangement
(3) Lossen rearrangement (4) Schmidt rearrangement
(5) Baeyer villigers oxidation (6) Beckmann rearrangement
(7) Bamford-stevens reaction (8) Chichibabin reaction
21. Carbon-carbon bond formation occur in the following
(1) Perkin condensation
(2) Benzoin condensation
(3) Clemmension reduction
(4) Cannizzaro reaction
(5) Stobbe condensation
(6) Claisen ester condensation
(7) Mc-Murry reaction
(8) Baeyer villigers oxidation
(9) Fries rearrangement
(10) Reimer-Tiemann Reaction

South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
 88

IIT-JAM CHEMISTRY 2023

TEST : NAMED REACTION & REARRANGEMENTS
Time 00 : 45 Hour Date : 29-09-2022
M.M. : 35

PART - A
1. (b) 2. (c) 3. (b) 4. (d) 5. (b) 6. (b) 7. (b)
8. (a) 9. (c) 10. (a)

PART - B
11. (a,b,c,d) 12. (b,c) 13. (a,c) 14. (a,c,d) 15. (a,b,c,d)

PART - C

16. (2) 17. (4) 18. (6) 19. (4) 20. (4) 21. (7)

South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455