VIGYAN VRIKSH

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TRUST BELIEVE ACHIEVE Reaction Intermediate DPP-1
1. Among the following, ESR active carbene is

(a) (b) :CCl2

N N
(c) :CPh2 (d) :C(OMe)2
2. In the following reaction, the major product P is
O
CH2N 2
OH P

O O O O

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

3. Among the following transformation which will NOT generate carbenes?

CN heat H Cl
N LDA
(a) (b)
N NC R Cl

(c) CCl3COONa heat (d) H 2CN2 h

4. Among the following carbenes, the most nucleophilic carbene is

Ph
OMe
N
(a) (b) :CH2 (c) :CCl2 (d) C
N F

Ph

5. In the following reaction, the major product P is

R H Br 1. BuLi (–115°C)
P
then (–90°C)
Br
Bu
(a) RCH2Br (b) (c) R H (d)
R Bu Br Bu

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6. In the following reaction, the major product P is
F3C N
h
P
N
R
CF CF3
(a) (b)
R R
H
N
N
F
(c) (d)
F
R
R
7. Among the following carbenes, the least stable carbene is

N N
(a) (b)
P Si P CF3
N N

(c) O O (d)
N N

+ N2CHCO2C2H5   A
SbCl5
8. Major product
; A is

NH2 O
CH 2CO2C2H5 NH–CH2CO2C2H5
(a) (b)

O N – CHCO2C2H5
CO 2C2H5
(c) (d)

Multiple Select Questions (MSQs)

9. Which among the following are Ambiphilic carbenes

(a) CH3O C
••
Cl (b) CH3O C
••
F (c) CH 3O C
••
OCH 3 (d) Ph C
••
Cl

10. Which among the following are nucleophilic carbenes.

(a) Cl CCl
••
(b) Ph C
••
Cl (c) CH 3O C
••
OCH 3 (d) H3C O C N

11. Which among the following method can be used to generate carbenes.

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VIGYAN VRIKSH DPP-(1) /Reaction Intermediate(NAT)
(a) Photolycis of AIBN (b) Photolysis of Diazoalkanes
(c) Photolysis of Diazirines (d) Photolysis of salts of sulfonyl hydrazone
12. The correct statement(s) about carbene is(are)
(a) Carbene is a neutral species
(b) Carbene is an intermediate in the Curtius rearrangement
(c) Carbene can insert into both  and -bonds
(d) Carbene is generated from amines on reaction with nitrous acid
13. Among the following ESR inactive carbene is:

(a) (b) : CCl2

N N
(c) : CPh2 (d) : C(OMe)2
Numerical Answer Type (NAT)
14. Number of unpaired electrons a singlet carbene is_____.
15. Number of unpaired electrons in a triplet carbene is______.
16. Bond angle of a linear triple carbene is (in degree) ______.
17. Degree of unsaturation of the final product of the following reaction is?
O
CO2Me

N2
NET + GATE
18. Match the correct electronic configuration of different carbene species
Carbene species Electronic configuration
(i) Bent triplet carbenes (A) 2
(ii) Singlet carbenes (B) r1r1
(iii) Linear triplet carbenes (C) 1r1
(D) r2

(a) (i)-(C), (ii)-(D), (iii)-(A) (b) (i)-(C), (ii)-(A), (iii)-(B)

(c) (i)-(D), (ii)-(A), (iii)-(B) (d) (i)-(A), (ii)-(B), (iii)-(C)
19. In the following reaction, the major product P is
O
O
Me N
N base
P
N
N
O Me
O
O O
Me
N NH2
(a) (b) H 2C N2 (c) (d) H2N
N
O O O

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VIGYAN VRIKSH DPP-(1) /Reaction Intermediate(NAT)
20. In the following reaction, the starting material S is
4-(C12H 25)PhSO2N 3 O
(CH3CH 2)3N N2
S Ph
O O O O O

(a) Ph OH (b) Ph (c) R NH2 (d) Ph CF3

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TRUST BELIEVE ACHIEVE Reaction Intermediate DPP-2
a OH
1. b
CH 2 I 2 / Zn  Cu
 A
Me
The reactivity of double bond for Simmons-Smith Reaction and major Product A?
OH
OH
(a) a > b, A = Me (b) a > b, A =
Me

OH OH
(c) b > a, A = Me (d) b > a, A = Me

OH
Me
2. CH 2 I 2 / Zn  Cu
 A
OH
What is the major product A

OH OH
Me Me
(a) (b)
OH OH

OH OH
Me Me
(c) (d)
OH OH
OH
c b a
3.
OH
The order of reactivity for Simmons-Smith Reaction?
(a) b > c > a (b) b > a > c (c) b > a = c (d) c > b > a

Me Me
O O
4. CH 2 I 2 / Zn  Cu
 A

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VIGYAN VRIKSH DPP-(2) /Reaction Intermediate(NAT)
What is the major product A
Me Me Me Me
O O O O
(a) (b)

Me Me
O O
(c) (d) None of these

OMe
OH
5. CH 2 I 2 / Zn  Cu
 A
MeO
The number of double bonds involve in cyclopropanation reaction and major product?

OMe OMe
OH OH
(a) 4, A = (b) 1, A =
MeO MeO

OMe OMe
OH OH
(c) 1, A = (d) 3, A =
MeO MeO

Me
H
b a
c
6.
OH
The order of Simmon-smith Reaction for double bonds?
(a) a > b > c (b) b > a > c
(c) a > c > b (d) a > b >>> c (c will not give the reaction)

OH

7.  1. PCC
2. CH 2 I 2 / Zn  Cu
A
OMe
What is the major product A?
OH O

(a) (b)
OMe OMe

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VIGYAN VRIKSH DPP-(2) /Reaction Intermediate(NAT)
OH O

(c) (d)
OMe OMe
OMe

CH 2 I2 N 2CHCO 2 Et
8. 
Zn / Ag
 A 
Cu(I)
B

OMe OMe OMe OMe

CO2Et
CHCO 2Et
(a) A is ; B is (b) A is ; B is

OMe
OMe OMe OMe
CH2COOEt
(c) A is ; B is (d) A is ; B is

EtO2C

Multiple Choice Questions (MCQs)

9. 
(3 mole)CH 2 I 2
Zn / Cu
(A) ; Compound (A) is

(a) (b)

(c) (d)

O HO

10. 
CH 2 ZnI2
 D ; D is
O Major product

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VIGYAN VRIKSH DPP-(2) /Reaction Intermediate(NAT)

O HO O HO O HO O HO

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

OH
CH3O

11. 
Zn (Cu )
CH 2 I2
 P ; P is
Major product

Me

OH OH OH OH
MeO MeO MeO MeO

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

Me Me Me Me
12. Major product formed in the given reaction is
O

OEt CH I

2 2
Zn  Cu

O O
OEt OEt
(a) (b)

O O

OEt OEt
(c) (d)

13. In the following reaction, the major product P is

CH 2I2, Zn-Cu
P
OH dry Et2O

(a) (b)
OH O

O
(c) (d)
OH

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VIGYAN VRIKSH DPP-(2) /Reaction Intermediate(NAT)
Multiple Choice Questions (MCQs)
14. Find major product in following reaction
CHBrICl
?
Mg
Br I H
(a) (b) (c) (d)
Cl Br Cl

Cl
15 Find major producrt (A) in following reaction.
CH2I2
(A)
Cu – Zn

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

16 Find major product (A) in following reaction.

OH
CH2I2
(A)
Cu – Zn

O OCH3 OH OH OH

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

17 Find major product (A) in following reaction.

OCH 3
CH2I2
(A)
Cu – Zn

O OCH3 OCH 3 OCH 3 OCH3

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

18. CH2I2
(A)
Cu – Zn

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VIGYAN VRIKSH DPP-(2) /Reaction Intermediate(NAT)

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

Multiple Select Questions (MSQs)

19. OH + CH I 
Zn(Cu )
Major product
22
H
Choose the correct statement(s) regarding the major product
(a) Degree of unsaturation of product is 2
(b) Product can show geometrical isomerism
(c) Compound formed has plane of symmetry
(d) Compound formed is optically active
20. Which among the statements is/are correct
(a) Singlet carbene reacts with cis-2-butene to give cis-isomer of cycloperopane
(b) Singlet carbene reacts with cis-2-butene to give trans-isomer of cyclopropane
(c) Triplet carbene reacts with cis-2-butene to give cis-isomer of cyclopropane
(d) Triplet carbene reacts with cis-2-butene to give mixture of cis and trans isomer
21. Which of the following reactions are correctly written.

C + +
(a) H H
triplet

C + +
(b) H H
triplet

C +
(c) H H
singlet

C +
(d) H H
singlet

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VIGYAN VRIKSH DPP-(2) /Reaction Intermediate(NAT)
NET GATE

Me

Me CH I / Zn Cu
22. 
22

P
Me

The possible product formed in the above reaction and number of sp2 hybrid carbon in the major product?
Me Me
Me Me
(a) and number of sp2 carbon = 3 (b) and number of sp2 carbon = 1
Me Me
Me
O Me O
Me Me
Me
Me
(c) and number of sp2 carbon = 3 (d) and number of sp2 carbon = 3
Me Me
O Me O Me
23. In the following reaction, the major product P is
H CH3 CHCl 3
P
(CH3)3COK
H 3C H

Cl Cl Cl Cl
H CH3 H H
(a) (b)
H 3C H H3C CH 3

CH 3
(c) (d) Both a and b
H3C CH 2 CH CH 3

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TRUST BELIEVE ACHIEVE Reaction Intermediate DPP-3
NET+ GATE + JAM
Multiple Choice Questions (MCQs)
1. What is the product (Q) of the following reaction?


CHFBrI
t  BuOK
(Q)

Cl Cl

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

Cl F
2. A rather interesting example of the Wolff rearrangement with 2-diazocyclohexanone in methanol is given below.
Identify the major product:

O
N 2 
CH3OH / light


O O
O
OCH 3 O
(a) CO2CH3 (b) (c) (d) C O H

OH
Me
CHCl3  NaOH Ph 3 P  CH 2 CH 3
3.   A   B ; B is

Me

OH H OH
H2
Me C C CH3 C CH 3
H
(a) (b)

Me Me

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VIGYAN VRIKSH DPP-(3) /Reaction Intermediate

OH O
Me Me
(c) (d)

Me HC C Me
HC C Me H
H

CCl CO Na, DME

4. 
3 2 ?
N reflux

H
H Cl
CCl2
Cl
(a) (b) (c) (d)
N N
N N
H H
5. The major product formed in the following reaction is

CHCl
N K  3
EtONa

Cl OEt
(a) (b) (c) (d)
N Cl N OEt N N
6. In the following reaction, the major product P is
O
CO2Me [Rh2(OAc)4
P
N2 CH 2Cl2

O O O
O
CO2Me CO2Me
CO2Me
CO2Me
(a) (b) (c) (d)

7. In the following reaction, the major product P is

h
P
MeOH
O
N2

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

O
OMe CO2Me CO 2Me CO2Me
8 In the following reaction, the major product P is
H H
H3C O [Rh2(OAc)4]
P
NH
O CO2Et
N2
H H O
H3C EtO2C
(a) O (b)
N
O H 3C
CO 2Et NH
O
EtO2C O O

(c) H3C (d) CO 2Et

NH
H
NH H3C O
O
Numerical Answer Type (NAT)
9. Degree of unsaturation of the final product of the following reaction is

O
h
MeOH
N2

10. In the following reaction, the major product P is

O
N2 i. h P
ii. 

O O OH
OH O
O
(a) (b) (c) (d)
OH
11. In the following reaction, the major product P is
MeO
BuLi
Cl P

Me Ph

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VIGYAN VRIKSH DPP-(3) /Reaction Intermediate
Ph
Me
Ph
(a) (b)
Me
OMe
OMe
MeO MeO
(c) (d)
Ph
Me Ph
12. Which of the following reaction can give chlorobenzene as a product?

(a) CHCl 3, OH (b) CHBrCl2, OH

(c) CHBr2Cl, OH (d) CHFClBr, OH

13. Ph 
h
 A  Intermediate B

Correct statement(s) is/are

(a) A is an aromatic compound (b) B is an aromatic compound
(c) Intermediate formed is carbene (d) A and B has same number of carbon atoms
Numerical Answer Type (NAT)

O
|| 1. SOCl2
  Product
14. R  C  OH 2. CH 2 N 2 (1 eq.) (R  C (n  2) H 2n 3 )
3. AgOH, 
4. H 2O
5. H 

if number of hydrogens in the product is 24. The value of n is

Cl 
(1) CH 2 N2 (2 eq)
 Major product
15. C (2)  , PhCH 2OH

O
Degree of unsaturation of the product is

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TRUST BELIEVE ACHIEVE Reaction Intermediate DPP-4
1. In the following reaction, the major product P is
Et
OMe C C
O Et
P
O N
H
O OMe
O Et O Et
(a) (b)
O Et O Et
N N
Et

Et MeO H Et
OMe C C
O
Et
(c) (d)
O N N
Numerical Answer Type (NAT)
2. Number of pi bonds in the final of the following reaction is

BF3OEt2
N2
O

3. Number of pi bonds in the final product of the following reaction is?

N2

O CF3COOH

MeO

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VIGYAN VRIKSH DPP-(4) /Reaction Intermediate
NET+ GATE
4. In the following reaction, the major product P is
O H NaOMe
N P
R H + N Ts Rh(II) catalyst
O N O O O
(a) (b) R (c) (d)
R CH 3 R N R
5. In the following reaction, the major product P is
O
H C H2C N N
P
CH 2Cl 2, –78°C
H
O O
(a) O (b) (c) (d)
O
6. In the following reaction, the major product P is
N2
h
O P
H
O

O O O
(a) (b) (c) (d)
O O
O O H
7. Degree of unsaturation of the final product of the following reaction is?
O
CO2Me

N2

8. Me 
N 2 CHCO 2 C 2 H5
Br3 , 25ºC
 A ; A can be
Me Me O

H H

(a) (b) Me CO 2C2H5

Me
Me Me N–NHCHCO2C2H5 Me Me O
H

(c) Me O C2H5 (d) Me O

Me Me Me Me
O
CO2C2H5

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VIGYAN VRIKSH DPP-(4) /Reaction Intermediate
9. In the following reaction, products P and Q have formed. The correct option for P and Q is
Ph Cl h
Cl P+Q

Cl
(a) P = Ph (b) P = Cl
Q= Q=
Cl H Ph Cl

Ph Cl Cl
Cl
(c) P = Q= (d) P = Q = : CH2
Ph Cl

10. In the following reaction, the intermediate I is

Me 3Si Me3Si
1. (COCl)2
Intermediate O
CO2H 2. CH2N 2 [I] Me3Si
3. CuBr
Me 3Si

N2

O O

(a) Me3Si (b) Me3Si

SiMe3 SiMe3

Cl
O Me3Si
(c) Me3Si (d)

SiMe3 Me3Si

11. In the following reaction, major product P is

O O
1. TsN 3, Cs2CO 3
O P
2. Cu(OAc) 2, heat, toluene

O O O O
EtO2C EtO2C EtO2C
(a) (b) (c) (d)

12. In the following reaction, the major product P is

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VIGYAN VRIKSH DPP-(4) /Reaction Intermediate

Ph
Rh2(OAc)4
N DCE/130°C
N P
O Ph
Ph

O Ph
O Ph
(a) (b) Ph
Ph
Ph

O Ph Ph

(c) Ph (d)
Ph O Ph

13. In the following reaction, the cyclopropane intermediate I is

MeO 2C
MeO2C
N2 cope
Rh2(OAc) 4 Cyclopropane rearrangement
intermediate
Me
OAc I Me OAc
O
O
MeO2C OAc MeO 2C H

(a) (b)
Me H Me OAc
O O

AcO
MeO 2C MeO2C H

(c) Me (d)
Me OAc
O
O

14. In the following reaction, the major product P is

i) CHBr 3, NaOH
Ph Ph P
ii) [H3O]+

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VIGYAN VRIKSH DPP-(4) /Reaction Intermediate

Ph Ph Ph Ph
Br
O O O
(a) Br (b) (c) (d)
Ph Ph Ph H

15. In the following reaction, the major product P is

O
O Zn/Cu
N P
CH2I2

O
N O
N
(a) O (b)

O
O O
N N
(c) (d)

Multiple Choice Questions (MCQs)

16. In the following reaction, the major product P is
O
i. h
N2 R3 P
R1 OR
R2
R4 ii. heat

OH O
O
R1 C R4 R1 R4 R1 O C
R1 R2
R4
(a) (b) (c) (d) R3
RO R3 RO R3 RO R3
R2
R2 R2 RO R4


Ph N N Ph P
17.
N2 R

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VIGYAN VRIKSH DPP-(4) /Reaction Intermediate

Ph
N
N N Ph
(a) Ph (b)
N R
R
Ph

Ph
H N
N R
(c) Ph N (d)
Ph N R

Ph

18. In the following reaction, the major product P is

O [Rh(II)]
N2 P
O
O O
O O
H O O H
(a) O (b) (c) (d) O
H H H H

19. In the following reaction, the major product P is

N O h P
+ Me2S
Ph O O

N O SMe2
(a) (b)
Ph O SMe2 Ph NH2

O
(c) SMe2 (d) Ph N
Ph N
20. In the following reaction, the major product P is
N2
CF3CO 2H
O P

MeO

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VIGYAN VRIKSH DPP-(4) /Reaction Intermediate
O
O

(a) (b)
O MeO
OCO2CF3

(c) O (d)
MeO
MeO
21. In the following reaction, the major product P is
O
[Rh2(OAc)4]
P
N2 Heat
CO2Et

O
O

(a) (b) O
CO2Et OEt

O O

O
(c) (d) O
H
EtO OEt

22 In the following reaction, the major product P and Q are

NHCO 2Bn i. EtOCOCI, Et 3N PhCO 2Ag
P Q
Ph ii. CH 2N2 Et 3N, MeOH
CO 2H

NHCO 2Bn NHCO2Bn

P = Ph Q = Ph CO 2Me
(a) N2
O

NHCO 2Bn NHCO 2Bn

P = Ph Q = Ph OMe
(b) N2
O O

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VIGYAN VRIKSH DPP-(4) /Reaction Intermediate
NHCO 2Bn NHCO2Bn
P = Ph O Q = Ph O
(c) N2
O O O

NHCO2Bn NHCO2Bn
P = Ph Q=
(c) N2 O
O
23. In the following reaction, the major product P is

1. CHCl3-KOH
HO OMe P
2. H2O2-NaOH

HO OMe HO OMe
(a) (b)
HO2C HO

HO OMe HO OMe
(c) (d)
CO2H OH
24. In the following reaction, the major product P is
i. [Rh2(OAc)4]
Ph N2 P

S
ii. PhCHO

O
O S O
Ph
(a) Ph (b) (c) HO (d)
Ph Ph Ph Ph Ph
O
Ph
25. In the following reaction, the major product P is
Me

O
i. Ph3P = CHCl
O Me P
Me ii. NaHMDS
O
OBn

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VIGYAN VRIKSH DPP-(4) /Reaction Intermediate

Me Me

O HO
Me Me
(a) O Me (b) HO Me

OBn OBn

Me

O O
(c) Me (d) Me
O O

OBn OBn

Multiple Select Questions (MSQs)

26. Which among the following statements are correct.
(a) Bent triplet carbene has ´ p´ electronic configuration
(b) Singlet carbenes has 2 electronic configuration
(c) Linear triplet carbens has p´ p´ electronic configuration.
(d) Singlet carbene has p2 electronic configuratio

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TRUST BELIEVE ACHIEVE Reaction Intermediate DPP-5
1. In the following reaction, the major product P is

TiCl4
(CH2)4 N N N P

Here the major product P is

O O
O
N
(a) HN (b) N (c) (d)
HN

2. In the following reaction, the major product P is

Br

O O N O
O
NH 2 P
DBU
O MeOH, reflux

O
O
O NH2
(a) O (b) O Br
O O

O O
O
(c) N (d) O N O
H
3. What is the Major Product of the Reaction?

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VIGYAN VRIKSH DPP-(5) /Reaction Intermediate
CO2H
H2SO4
?
NaN3
H3 C CH3

NH3 CoNH2

(a) (b)
H3 C CH3 H3 C CH3

COOR COOH

(c) (d)
H3 C CH3 H3 C CH3

4. Complete the Reaction and give Major Product?

NaN3
Ph CH2 COOH ?
H2SO4
(a) Ph CH2 NH2 (b) Ph NH2 (c) Ph CONH2 (d) Ph CH2 CH2 NH2
5. What is the Major Product ?
O
C NH2
Br2
?
N F KOH

NH 2 O
NH2
NH C OH
(a) (b) (c) (d)
N F N F
N F N F

6. What is the Major product of the given Reaction ?

O
NBS
R C NH2
CH3OH
NaOCH3

O
(a) (b) R NH2 (c) R COOH (d) RNHCO2CH3
R C OCH3
7. What is the Major Product of the Reaction?

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O
H+
R C OH N3H ?

O
(a) R NH2 (b) (c) R CH2 NH2 (d) R COOH
R C NH2
8. In the following reaction, the major product P is
O
h, benzene
P
EtO N [H +]
NHCO2Et

(a) (b) N CO 2Et

O
(c) N CO 2Et (d)
EtO NH 2
9. What is the Major Product?
O
TiCl4
PhN3 ?

O O O
CONH2
N Ph N Ph
(a) (b) (c) (d) O
N
Ph

10. What is the Major Product?

N OH
H
R C ?
R´

O O O
(a) R NH C R´ (b) R C NH R´ (c) R C R´ (d) R NH2
11. Complete the Reaction sequence.
CH 3
C NOH
P-toluene sulf onyl
?
chloride
H Py

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NHCOCH3 CONHCH3 NH2 NHCOOH

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

H H H H
12. Complete the Reaction Sequence ?
NOH
HCl
C C(CH3) ?
CH3CO2H

O
NH2 NH C CH3
(a) (b)

O O
(c) C NH C(CH3)3 (d) NH C C(CH3)3

13 What is the Major Product of the Reaction?

O
(i) NaN3
CH3 (CH2)10 C Cl ?
(ii) benzene 70°C

H
CH3 (CH2)10 N C OH
(a) CH3 (CH2)10 N C O (b)
O

H
CH3 (CH2)10 N C CH3
(c) CH3 (CH2)10 NH2 (d)
O

14. Complete the Reaction Sequence?

NaN3
?
CF3CO2H
O

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NH O
(a) O (b) (c) (d) N
O O
NH2 O NH
H

15 What is the Major Product of the Reaction sequence?

H3CO2C CH3
(i) NaN3 / 80°C
N Ph ?
(ii) MeOH
H3CO2C COCl

H3CO2C CH3 H3CO2C COOH

N Ph N Ph
(a) (b)
H3CO2C NHCO2CH3 H3CO2C COOH

H2NOC CH3 H3CO2C CH3

N Ph N Ph
(c) (d)
H2NOC CO2H H3CO2C NH2

16 What is the Major Product?

CH2CH3
(i) SOCl2 / Py
H3C C CO2H ?
(ii) NaN3 / 
Ph Xylene

CH2CH3 CH2CH3
O
H3C C CO NH2 H 3C C NH C OH
(a) (b)
Ph Ph

H2C CH3 CH2CH3

H3C C NH2 H3 C C NH COCH3

(c) (d)
Ph Ph

17. Complete the Reaction sequence?

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HO 2C (i) SOCl2
(ii) NaN3
Ph
(iii) heat
(iv) H / H 2O

COOH
H3N Cl H2NOC HN
(a) (b) Ph (c) (d) Ph
Ph Ph

18. Complete the Reaction sequence ?

O tC4H9
H3CO2C CONH2 Pb(CO2CH3)4
?
t-BuOH
O O

H3C CH3

t
O C4H9
t
H3CO2C NHCO 2 t
C4H9 O C4H9
H3CO2C CONH2
(a) O O (b)
HO OH
H 3C CH3

t t
O C4H9 O C4H 9
H3CO2C NH2 HOOC NH2

(c) O O (d) O O

H3C CH3 H3C CH3

19. Complete the Reaction sequence of the given Reaction?

O TiCl4
?
(CH2)4N3

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O O
(a) (b)
(CH2)4 NH2 (CH2)3 COOH

O O

N N
(c) (d)

20. What is the Major Product of the Reaction?

PCl5
?
NOH
H3 C CH3

CH2CH2CN CH2 CH2 COOH

(a) C CH2 (b) CH CH3

CH3 CH3

CH2 CH2 CN

(c) CH CH3 (d) NH2

CH3 H3 C CH3

21. What is the Major Product of the Given Reaction sequence?

(i) N2H 4 (2 eq.)
H 3C2O2C(CH2)4CO2C2H 5 ?
(ii) HNO2
(iii) 
(iv) H / H2O

(a) H5C2O2C(CH2)4  NH2 (b) ClNH  (CH )  NH Cl

3 2 4 3

C2H5 C (CH2)4 C C2H5

H2N C (CH2)4 C NH2
(c) (d) N N
O O OH
HO
Multiple Select Questions (MSQs)
22. Which among the following are examples of Bechmann rearrangement
Et Et
1. SOCl2 Py
(a) C COOH C NH 2
2. NaN 3
Ph Ph

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H+
(b) NH
NOH
O

OH O
(c) O N O
NH

O NH 2

(d) NH 2

23. Which of the following statements are incorrect regarding the given reaction.
COOH
H 2SO4
NaN3
(H 3C)3C C(CH3) 3
(a) Reaction involves carbene (b) Final product contains oxygen
(c) Final product is not-aromatic (d) Final product contains nitrogen
24. Products formed during the following reaction is/are
Ph
Me Ph
H+
+
N N
OH OH

O O Me Ph O Ph
Ph
(a) NH (b) Ph NH (c) (d) NH
N
OH
25. An isocyanate can be formed using:
(a) wolf rearrangement (b) Lossen rearrangement
(c) Curtius reaction (d) Schmidt reaction
26. Which of the following reaction involves nitrene

O Cl–
HOOC (1) EtOC Cl , NaN3 H3N
(a) Ph (2)  Ph
(3) H+

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NOH O
HCl (CH ) C C N
(b) C C(CH 3)3 3 3
H

O
O
TiCl4
(c) N
(CH2) 4N 3

O CH 2Ph
h H3CO2C CH 2Ph
(d) N2
CH3OH

27. In which of the following reactions a nitrene intermediate is formed?

(a) Curtius reaction (b) Schmidt reaction
(c) Wolff rearrangement (d) Favorkii rearrangement
Numerical Answer Type (NAT
28. Number of pi-electrons in the final product of the following reaction is


N3
29. Degree of unsaturation in the final product of the following reaction is?

PCl 5
NOH

30. Number of oxygen atoms present in the final product of the following reaction is ____.

O NBS
RCNH2 CH3OH
NaOCH 3

NET + GATE
Multiple Choice Questions (MCQs)
31. In the following reaction, the major product P is

OSO 2NH 2

Rh(II) (2 mol%)
P (Casacade product)
PhI (OAc)2 (1.1 equiv)

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O O
S NH
O O O O O O O
S Ph S NH S Ph
Ph
(a) O N (b) O (c) (d) O

32. Among the following, which transformation does NOT provide nitrene?
O R NO2 PR
h or heat 3
(a) O (b)
O N
PhCONH2 h O
Ph
(c) (d) N
Ph Ph

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TRUST BELIEVE ACHIEVE Reaction Intermediate DPP-6
NET+ GATE
1 In the following reaction, the major product P is
IN3
S
S DCM/CH 3CN
–78°C
P
H+

H NH2 O
O
N NH
N
(a) (b) (c) (d)

O
Pb(OAc)4, K2CO3
N NH2 + P
2 DCM
O
O

N
(a) NH (b)
O
O

N N
(c) (d)
HN
O
3. In the following reaction, the major product P is
PhI (OAc)2
MgO
O NH 2
Cat. Rh(II)
O

O H O
O
HN N O N
(a) O (b) (c) N O (d) O
O H

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4. In the following reaction, the major product P is

O
OH
N3
H P
H+, heat

NO2

N
O O
N
OH
N N
(a) H (b)

NO 2 NO2 OH
OH
NO2
N N
(c) O (d) HO NO 2

5. In the following reaction, the major product P is

O Rh2(OAc) 4
PhI N P
S O
O
O
O
O
O O H
N S O
S
HN O O
(a) (b)
Ph CO 2Et CO2Et
H O
N S O
O O
(c) (d) None of these
O

Ph
6. In the following reaction, the major product P is
O
O
S
N
P
heat

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Ts H Ts
N N N
(a) (b) (c) (d)
NH

7. In the following reaction, the major product P is

1. TMSN3/KN3
Cl P
heat
O +
2. H / H 2O

NH
(a) (b) N C O
O

NH2
(c) (d) NH2
O
Multiple Choice Questions (MCQs)
8. In the following reaction, the major product P is
O O Rh(II)
S P
O NH2 PhI (OAc)2
H MgO

O O
O S
O HN O
S
(a) N O (b)
Ph H
Ph
O O O O
H
HN S N S
O
(c) (d) Ph O
Ph
9. In the following reaction, the major product P is
Cat. Rh(II)
P
Ph Heat
N3
Ph
Ph
H
N N
(a) Ph (b) (c) (d)
N
H N N NH2
H

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10. What is the Major Product ?

H3C
Polyphosphoric
?
acid
NOH
H

H3C H 3C CH3 HOOC

NH
(a) (b) (c) (d)
N O NH2 NOH
H H H H O H

11. Complete the Reaction sequence ?

(i) Pb(OAc)4 / MeOH
CH2CONH2
(ii) OsO4

CH2CO2H
CH2NHCO2CH3
(a) HO (b)
OH OH OH

CH2 O C NH CH3 CH 2NHCO2CH3

(c) O (d)
OH OH OH OH
12. In the following reaction, the starting material S is

Co2Me
Rh2(OAc) 4, heat N
S OMe
H 3C N O

N3
(a) MeO2C CO2Me (b)
MeO2C CO2Me

N2 N2
(c) (d) O
MeO2C CO 2Me MeO2C

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13 In the following reaction, the major product P is
O
Cu[CH(COCF3) 2]2
F
Me O N2 CH Cl
2 2
ref lux
O O O O

(a) Me O (b) Me O (c) H2C O (d)

Me O

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TRUST BELIEVE ACHIEVE Reaction Intermediate
ANSWER KEY
DPP-1
1. (c) 2. (c) 3. (a) 4. (a) 5. (c) 6. (b) 7. (c)
8. (c) 9. (a,b) 10. (c,d) 11. (b,c,d) 12. (a,c) 13. (a,b,d) 14. (0)
15. (2) 16. (1800) 17. (4) 18. (b) 19. (b) 20. (d)
DPP-2
1. (a) 2. (a) 3. (a) 4. (c) 5. (b) 6. (a) 7. (d)
8. (c) 9. (a) 10. (a) 11. (d) 12. (d) 13. (a) 14. (d)
15. (c) 15. (c) 17. (c) 18. (b) 19. (a,b,c) 20. (a,d) 21. (a,b,c)
22. (a,c,d) 23. (a)
DPP -3
1. (d) 2. (a) 3. (a) 4. (b) 5. (c) 6. (b) 7. (c)
8. (a) 9. (3) 10. (a) 11. (b) 12. (a,b,c) 13. (a,c) 14. (12)
15. (11)
DPP -4
1. (b) 2. (2) 3. (4) 4. (b) 5. (c) 6. (a) 7. (4)
8. (b) 9. (b) 10. (b) 11. (d) 12. (c) 13. (b) 14. (b)
15. (b) 16. (b) 17. (b) 18. (d) 19. (c) 20. (a) 21. (c)
22. (a) 23. (b) 24. (d) 25. (a) 26. (a,b,c)
DPP -5
1. (b) 2. (d) 3. (a) 4. (a) 5. (c) 6. (d) 7. (a)
8. (a) 9. (b) 10. (a) 11. (a) 12. (d) 13. (a) 14. (b)
15. (a) 16. (c) 17. (a) 18. (a) 19. (d) 20. (a) 21. (b)
22. (b,c) 23. (a,b,c,) 24. (a,b,c,d) 25. (a,b,d,) 26. (a,b,c,d,)
27. (a,b) 28. (14) 29. (7) 30. (2) 31. (c) 32. (c)
DPP 6
1. (b) 2. (c) 3. (a) 4. (a) 5. (a) 6. (c) 7. (d)
8. (b) 9. (a) 10. (c) 11. (a) 12. (c) 13. (a)

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