PART 1

1. Find out the total number of stereoisomers of 3,6-Dimethyloct-4-ene

(A) 8 (B) 7 (C) 6 (D) 4

2. Find out the total number of stereoisomers of 3-bromo-6-chlorooct-4-ene

(A) 8 (B) 7 (C) 6 (D) 4

3. Which of the following compound will racemise on keeping in aqueous solution .

O O O
Me Me
D O
Me Ph Ph
H CH3 CH3
(A) D (B) H (C) Et (D) Ph CH3

4. P (C6H10O2) is an optically active dicarbonyl compound which significantly exists in optically

inactive enol form. Identify P.

O O O O O O

C C C
H3C H Et H H3C CH3
(A) Et (B) Me (C) Me (D) None of these

5. Compare rate of SN1 reaction or solvolysis :

Cl Cl Cl
Br Br Br

(i) (ii)
O
(a) (b) (c) (b) (c)
(a)

Br Br Cl I Br I

(iii) (iv)
(a) (b) (c) (a) (b) (c)

Ph
Ph Me
Cl
(v) Ph CH2 Cl Ph Cl (vi) O Cl Cl
Ph Me Me
(a) (b) (c) Ph (b)
(a)

TsO TsO TsO

OTs
(vii) (viii)

(b) (a) (b)

(a)
 Br Br

Cl Cl O
(ix) (x)

(a) (b) (b)

(a)

Br Br

(xi)

(a) (b)

O O

Me CH2 O S Me Me CH2 O S CF3

(xii)
O O
(a) (b)

Ph Ph

(xiii) Ph
I Cl
I I
(a) (b) (c) (d)

F
CH3 CH3 H3 C CH3
(xvi) F Ph Br
Br Br Br
(a) (b) (c) (d)
PART 2
1. Find out the reactivity order of SN2 reaction :

Cl Cl Cl

(i)

NO 2 Me
(a) (b) (c)

Me Me
(ii) Me Cl
Me Cl Me Cl Me Cl
Me

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

Br

Br Br

(iii)

(a) (b) (c)

O
(iv) O Cl
H3C Cl H3C Cl
H H3C Cl
(a) (b) (c) (d)

Br

(v) Br Br N C CH2 Br Me Me Me Br
(a) (b) (c) (d)

2. Find out the product of the given reaction :

H Cl

NaI / acetone
(i)
H t-Bu

O
Br
(ii) O Me NaI / acetone
D
T
 O

(iii) H NaI / acetone

O
TsO
D

H2C CH CH3
(i) Ph-CH2-S
(iv) O
(ii) H+

Ph
I
NaOH
(v)
Me H

Br
H

Me
NaCN
(vi)

3. Which of the following correctly indicates the order of reactivity of the halides below with
sodium iodide in acetone ?

Br CH2Br CH2Br

(I) ( II ) (III)

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

4. Which one of the following undergoes nucleophilic substitution with NaCN at the fastest rate ?

Br Br
(A) CH3 (B) CH3

Br
CH3
Br CH3
(C) (D)

CH3
H3C
5. F
for the following compound represented by the Newman projection
(staggered) above, what is the dihedral angle between the methyl groups in the conformer that
has the smallest molecular dipole moment ?
(A) 00 (B) 300 (C) 600 (D) 1200
6. Find out the structure of those compound which give only two monochloro product of the
given molecular formula is C8H16

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

PARAGRAPH QUESTION( Q.No.7 and 8 )

conc.H2SO4
HO P

7. How many 1,2-shifts are possible in the given following reaction:

(A) 3 (B) 4 (C) 5 (D) 6

8. Major product ‘P’ of the reaction is:

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

9. Which of the following compound SN1 & SN2 reaction can take place.
Cl Cl
Cl Cl

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

10.
NaI / Acetone
Br (P)
Cl

Major product ( P ) is :

I I
Cl I
(A) (B)

Br
I Cl
(C) (D)

11.
Cl Cl

Total number of stereoisomers of the given compound is :

(A) 1 (B) 2 (C) 3 (D) 4
12. The gauche interaction values for
Me /Me 3.3 KJ / mol
Me / Br 0.8 KJ /mol
Br / Br 3.0 KJ /mol
Respectively. Among the following the most stable conformation of 2, 3 – dibramobutane is
Br Br Br Br

Me Br H Me H Br Br Me

Me H Me H Me H Me H

(A) H (B) Br (C) Me (D) H

13. Which of the following compound does not show geometrical as well as optical isomerism.
H
CH3 H
Br N O
N H
H H D
N D
H
N D H O N Cl
(A) D (B) H (C) D (D) H

14. Which of the following compound will not be stabilized after deprotonation
CF3

F 3C CF3
O

(A) (B) O (C) (D) F 3C CF3