SIKKIM UNIVERSITY

Department of Chemical Sciences

Organic Chemistry I: CHE-PG-C102
Unit -2 : October 12, 2015
Dr. B. G. Roy
Total Marks: 25

Time: 1 h
Section A
Answer all questions (5 x 1 = 5)

1. Stereoisomers I and II undergo E2 elimination on treatment with sodium ethoxide in ethanol.

One isomer reacts 500 times faster than the other. Also, one isomer gives X as the only product,
whereas the other gives Y together with some X
Which of the following statements provides the best assignment of I and II?

A) II reacts faster and gives both Y & X

B) II reacts faster and gives only X
C) I reacts faster and gives both Y & X
D) I reacts faster and gives only X
2. What is the expected order of reactivity of the following compounds in electrophilic nitration?
(more reactive > less reactive)

A) I > II > III > IV

B) IV > III > II > I
C) III > IV > I > II
D) II > I > IV > III
3. Which of the following is the major product from bromination of meta-nitrobenzenesulfonic
acid?

4. Which of the following is the major product from this reaction?

1. Which is the correct structure combination of A and B.

CO2H

CO2H

CO2H

Na

Liq. NH3
OMe

OMe

HBr (1 Eqv)
II

A)

B)
CO2H
Br
OMe
II

OMe

CO2H

II

CO2H

I
C)

Br
OMe

CO2H

OMe
CO2H

I
D)

OMe
Br II

CO2H
Br

II

Section B
Answer any Two (2 x 10 = 20)
5. a) Which product do you expect from following reaction and why?
2

b) Explain the difference in major products following reactions?

2

OMe

OMe

c) Explain the difference in product formation with temperature in following

reaction?
2
Me

Me

Me

Me

Me
+

CH3Cl, AlCl3

CH3Cl, AlCl3

160 oC

40 oC

Me

Me

d) What product do you expect from following reactions? give reason for your
answer.
2

e) How will you explain following difference in products show with mechanism.
2
F
D

F
KNH2
NH3 (l)

Br
H

KNH2

NH2

NH3 (l)

1. How will carry out following transformations? Give mechanism in each case.

a)

b)

Write appropriate reagents and products for following organic transformations?

Give mechanism in each cases?

a)

b)

2.

Section B
Answer any 3 questions. (3 x 10 = 30)
1.a) Write the structure of A, B and C. Write reason for your choice in each case.
3
O
A
O

O
O

Cl

B
C

Cl

c) Write the structure of A and B. Mechanism of the formation of B. How will you
make A?
4

2. a) Write the structure of A and B? Give mechanism of their formation.

3
O2N

NaOMe

Cl
O2N

NaNH2

Cl

b) This is the stepwise process of reductive amination. Give structure of A and B.

2
O
Pr

MeNH2
H

NaBH4

Or NaBH3CN

d) Explain the difference in product formation with temperature in following

reaction?
2
Me

Me
Me
+

Me

Me
CH3Cl, AlCl3
40 oC

CH3Cl, AlCl3
160 oC

Me

Me

4. a) LiAlH4 is very useful for formation of amine from amide but not ether from
ester.- Give reason.
OR Explain following reactions
3

Me
Me

LiAlH4
N
H

Me
Me

LiAlH4

Me

N
H

Me

Me
Me

c) How will you carryout following conversion?

4
NO2

CH3

Br
CO2H

OH OH