Chemistry by Prof.

Ajay Y Kapoor Sir

TOPIC : REACTION INTERMEDIATE : SINGLE TYPE QUESTIONS


OH Trans 2 butene
Q.1 CHF2Br  (A)      (B)
(Intermediate)
in this reaction B is:

(A) (B) (C) (D)

CH N ( 2 mole ) Ag O ,
Q.2 22  2
 (X)
MeOH

Product (X) of above reaction is

(A) (B) (C) (D)

O
||
Q.3 CH 3  C  CH 3 CH
2
N2 CF CO 3H
 (X) 3   (Y) (Major)

Product (Y) is
O O
|| ||
(A) CH 3  C  O  CH 3 (B) CH 3  C  O  CH 2  CH 3

O
||
(C) CH 3  CH 2  C  O  CH 3 (D) CH3– CH2– CH2– O – CH3

Q.4 Correct order for rate of carbylamine reaction for following compound will be :

(I) (II) (III)

(A) II > III > I (B) II > I > III (C) III > II > I (D) I > III > II

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 Chemistry by Prof. Ajay Y Kapoor Sir
I
| HBr
Q.5 PhCHCl  B 
A EtOK  C
correct presentation of C is:

(A) (B) (C) (D)

Q.6 +   ?
MeOK

(A) (B) (C) (D)

Q.7 Which of the following will not give carbylamine reaction

CH 3 NH2
|
(A) CH 3  C  NH 2 (B)
|
CH 3
(C) CH 3  CH 2  CH  NH 2 (D) CH3–NH–CH3
|
CH 3

 CHCl
Q.8 H (X) 3  (Y) Major
OH  KOH , 
N
H
Product (Y) is

Cl CO2H
(A) (B) (C) (D)
N Cl N N
N
CHO H

Q.9 Predict the product of the diazoketone with silver (I) benzoate.

PhCO Ag
 2
Et 3 N

(A) (B) (C) (D)

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 Chemistry by Prof. Ajay Y Kapoor Sir

( i ) CH N ( 4 mole)
Q.10  22  
 (A)
(ii ) Ag 2O;  / MeOH

Product (A) of above reaction is:

(A) (B) (C) (D)

Q.11 A rather interesting example of the Wolff rearrangement 2-diazocyclohexanone in methanol.

Suggest major product

CH OH / light
3 

(A) (B) (C) (D)

Q.12 Major product of this reaction is CH 2=CH–CH2–CH2–CH2– MeLi

 ?
Et 2O

(A) (B)

(C) (D)

F
CH Cl
Br
Q.13 Product (major)
KOH

Which of the following is correct product for the given reaction:

F
(A) (B) (C) (D)
Cl
Cl Br

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Q.14 Triplet carbene is

(A) a Diamagnetic species (B) a Paramagnetic species
(C) Nucleophile (D) Species having zero dipole moment

Q.15 What is the product of the following reaction?

MeOK
  ?
in chloro form


(A) (B) (C) (D)

Q.16 Write the number of minimum carbon atoms required for chiral molecule in following compound.
(i) A chloroalkane (ii) An alcohol (iii) An alkene (iv) An alkane
(A) 5, 5, 5, 8 (B) 5, 4, 5, 7 (C) 4, 4, 6, 7 (D) 4, 4, 4, 6

aq. KOH
Q.17 Me–CH = CH2 + CHCl3    A (Major products) is
excess , 

O OK
(A) (B) OH (C) (D)
O OK O
OH

HBr
Q.18 PhCHCl2  B 
A EtOK  C
correct presentation of C is:

(A) (B) (C) (D)

Br KOH
Q.19 2   A (Major)

Product (A) is:

(A) (B)

(C) (D)

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 Chemistry by Prof. Ajay Y Kapoor Sir

O
|| CH N 2 CH CO 3H
Q.20 CH 3  C  CH 2  CH 3 2 A (Major) 3   B (Major)
Product B is:
O O
|| ||
(A) CH 3  O  C  CH 2  CH 2  CH 3 (B) CH 3  C  O  CH 2  CH 2  CH 3

O O
|| ||
(C) CH 3  CH 2  C  O  CH 2  CH 3 (D) CH 3  C  O  CH 2  CH 3

NH2
CHCl / KOH
Q.21  3  Compound having unpleasant smell.
CH3

NO2 CN NC NH–CH3

(A) (B) (C) (D)

CH3 CH3 CH3 CH3

Q.22 PhCHCl2 A SbCl

5  B
correct presentation of B is:
Ph Ph Ph
[SbCl6]¯
(A) Ph – C [SbCl6]¯ (B) Ph

Ph

Ph Ph
 [SbCl6]¯
(C) ( D )
Ph
Ph Ph
 [SbCl6]¯ + Ph – Cl

O Me
|| *
Q.23 Ph  C  NH 2 + H D Br / KOH
2   ?

CONH2
Which of the following statement is incorrect reagarding the given reaction ?

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 Chemistry by Prof. Ajay Y Kapoor Sir
Me
*
(A) Ph N H 2 and H D are produced.
NH2

Me
(B) Cross over products PhNH2 and H D are also produced.
*NH2
(C) Migration of –R(alkyl group) of R–CONH2 takes place with retention of configuration
Me
*
(D) PhCO N HBr and H D are the intermediates formed.
CONHBr

OH
(i) CHCl3+KOH
Q.24 Major product
(ii) H3O
D D

OH
OH OH OH
CHO CDO
(A) (B) (C) (D)
D D
D D CHO D D CDO

REACTION INTERMEDIATE : MULTIPLE TYPE QUESTIONS

Q.1 Which of the following will not give Hoffmann bromamide reaction?
O O
|| ||
(A) CH 3  C  NH 2 (B) Ph  C  NH 2

O O
|| ||
(C) CH 3  C  NH  CH 3 (D) Ph  C  NH  Ph
Q.2 Which one of the following carbocation would you expect to rearrange.

(A) (B)


(C) Ph  CH 2  CH  CH 3 (D)

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Q.3 In which reaction carbon skeleton rearrangement takes place:
CH 3
|
C  H ( i ) O 2
 Products
(A) | ( ii ) H  / H 2 O
CH 3

CH 3
|
(B) H 3C  C  CH  CH 2 Br
2 / Products
CCl 4
|
H
( i ) SOCl 2 , (ii ) CH 2 N 2
(C) H 3C  CH 2  C  OH     
(iii ) Ag 2O /  , H 2O
||
O

CH 3
|
(D) H 3C  C  CH  CH  CH 2  OCH 3 HCl


|
H

Q.4 Which of the following reactions are correctly represent the product(s) ?
O
C COONa
NaOH/Br2
(A) N—H
C NH2
O

OCH3 OCH3
(B) (i) PhLi
(ii) H2O
Ph
Cl (Major Product)

O
14
(C) 14 C–Cl 1. NaN3 NH2
2. OH¯/H3O/
O
1. AgOH
(D) CH3–CH=CH–C–OH CH3–CH=CH2
2. Br2/CCl4/

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 Chemistry by Prof. Ajay Y Kapoor Sir
Q.5 Which of the following reaction is not representing major product.
O
 ||
(A) H CH3 C  NH  CH 3


14
(B) Ph Li C C CH3


O
|| Br2
(C) Ph  C  NH 2 
 Ph–NH2 (D) 
3 
HN
KOH H 2SO 4

O3 MeMgBr H2O SOCl2 (1) CH2N2

Q.6 P1 P2 P3 P
H2O 2 eq. H+ 1 eq. (2) Ag2O/ 4
CF3CO3H

What is correct about P1 to P4 ?

(A) P4 is a lactone.
(B) P1 can give iodoform reaction.
(C) P3 on heating can give preceding homologue of P 4.
(D) P1 and P2 both can give effervescence of CO2 with NaHCO3.

Q.7 Select correct statement for the given reaction.

O
|| Br2
Et  C  NH 2  (P1) Product (Major)
KOH
(A) Product (P1) will give alcohol as major product on Diazotization.
(B) Product (P1) can give positive carbylamine test
(C) Product (P1) will give a tetra alkyl ammonium halide salt when treated with excess of Et–Br.
(D) Product (P1) can be prepared by Curtius reaction of EtCOCl with NaN3 followed by hydrolysis.

Q.8 Which of the following reaction is not representing major product.

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 Chemistry by Prof. Ajay Y Kapoor Sir
O O

(A)
NH Br

2 OH
KOH / H 
O2 N O2N NH2
O

H
14

(B) C=C LDA

 14


OTs

OH O
C=N PCl5
(C) 
 C–NH–CH3

H3C

(D) HN

3 
H 2SO 4

O
N2
(i)  (i) SOCl2
(A) (B)
Q.9 (ii) HOH (ii) NH2–NH2
(iii) NaNO2/HCl,
Which is / are correct statement(s) about the product (A), (B) and involved reactions ?
(A) Product (B) gives iso cyanide test.
(B) Product (A) is a carboxylic acid containing six carbon atoms.
(C) Rearrangement is the RDS during formation of (A) and during formation of (B) from (A).
(D) Arndt Eistert, Curtius, Diazotisation reactions are involved in above interconversion.

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Q. No. Answer Key Q. No. Answer Key

1 C 1 C D

2 C 2 B C
3 A C
3 B
4 A C
4 A
5 A B D
5 C
6 A B C D
6 A
7 A B C D
7 D 8 B D
8 B 9 A C
9 D

10 B

11 A

12 C
13 C

14 B

15 C

16 C
17 D

18 C

19 D

20 B
21 C

22 C

23 B

24 A

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