Time : 1 hrs Max.

Marks: 79
Single correct [6 × 5=30]
O CH 2  Ph O Me
|| | || |
Q.1 HOOC  CH 2  NH  C  CH — NH  C  CH  NH 2
What will be the correct representation of the above tripeptide.
(A) Gly-Phe-Ala (B) Ala-Gly-Phe (C) Gly-Ala-Phe (D) Ala-Phe-Gly

(i ) LAH
SOCl2 (ii ) H3O
Q.2 4-Pentenoic acid  (X) (Y)   (Z)
(iii ) dil OH
Identify final (major) product:
O
||
(A) CH 2  CH  CH 2  CH 2  C  N (B) CH2=CH–CH2–CH2–CH2–N

OH
|
(C) CH 2  CH 2  CH 2  CH 2  CH  N (D) CH3–CH2–CH2–CH2–CH2– OH

Q.3  X. X will be


(A) (B) (C) (D) None

Q.4 Suitable reagent(s) to convert acetyl chloride into acetaldehyde is / are :

(a) Na–C2H5OH (b) NaBH4 (c) H2/Pd–BaSO4 (d) LiAlH (CMe3)3
(A) a, b, c (B) c, d (C) b, c, d (D) a, b, c, d

O 18
Q.5 || + H–O HCl
 (X)
Ph  C  O  H 
Major product (X) is.
18
O O O
18
(A) Ph–C–O (B) Ph–C–O (C) Ph–C–O (D) Ph–O

Page No.1
  
Q.6 EtO
 A H3O B Zn
(Hg)
 C
 HCl

C is:

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

Comprehension [3 × 3 = 9]

Comprehension (Q.7 & Q.9)

Dr. Sandy Robertson worked out following reaction sequence.

Br alc.KOH
NBS

alc.KOH
 (A)  (B) 2  (C)   (D) HgSO
 4  (E)
CCl NaNH
4 dil. H SO
2 2 4

KOH
(G) excess
 (F)
Q.7 Select true statement(s):
(A) when D is treated with D2 Pd BaSO4 it gives cis alkene.
(B) when D is treated with Na liq. ND3 it gives trans alkene.
(C) both
(D) none

Q.8 True about E is:

(A) It gives positive Fehling test.
(B) It does not give positive test with Braddy's reagent.
(C) It gives positive Iodoform test.
(D) It gives effervescence with NaHCO3.

Q.9 G is:

(A) Ph  C  CH (B) Ph  C  CHO

|| ||
O O
(C) Ph  CH  CHO (D) Ph  CH  COOK
| |
OH OH
More than one may be correct [3 × 3 = 9]

Q.10 HgSO4 / H2SO4 and B2H6 / NaOH H2O2 will give same major product, when react with which of the
following.
(A) O2N– C  CH (B)
H
(C) (D)

Q.11 In which of the following case configuration about chiral C* is retained:

Na CH Br SOCl CH ONa
(A)  3 (B) 2  3

PCl CH ONa H  / MeOH

(C) 3  3 (D)   


Q.12 Final product of which of following reaction give positive iodoform test.

(A) + CH3MgBr (1 mole)  (a)

O
||
(B) CH 3  C  O  Et + PhMgBr (1 mole)  (b)

O
||
(C) Cl  C  Cl + CH3MgBr (excess)  

(c)
( 2) H

O O
|| ||
(D) CH 3  C  O  C  CH 3 + PhMgBr (excess)  

(d)
( 2) H
2 Match the column [2 × 8 = 16]

Q.13 Column I Column II

O NO2

CH2 – C – O
(A) (P) Positional isomers
OH

O NO2

O– C – CH2 (Q) Metamers

OH

(B) (R) Geometrical isomers

C C
T C–O–C–C=C H C–O–C–C=C
(C) C=C C=C (S) First is Z and second is E.
H D T D

Q.14 Column I Column II

(Product differentiate by)
O3
(A) CH3–CH=CH2 
Zn
(U) + (V) (P) By Haloform test

CH 3
|
O3
(B) CH 3  C  CH  CH 3  (W) + (X) (Q) By Fehling test
Zn
O
|| 
(C) Ph  C  O  Ph H (Y) + (Z)
3O (R) By aq. NaHCO3

(S) By Tollen Test

Subjective [5 × 3 = 16]

Q.15 Cyclohexane-1,4-dione is a polar compound, having dipole moment value of 1.2 D. If mol
fraction of its chair form is 0.80, what will be the dipole moment of twisted boat form?

Q.16 Number of meso isomer of the given compound is

Br Br
C
C

Br Br

Me
H D
Q.17 Number of optically active isomer of H D
H D
Me

Q.18 Total number of geometrical isomer possible for

PhNHNH
Q.19 2  ?
  
( Excess)

Total how many osazones are obtained in this reaction sequence (z).
 Answers
1. D 2. B 3. C 4. B

5. A 6. C 7. A 8. C

9. D 10. A, B, C 11. A, C 12. A, B

13. (A) Q, S (B) P,S (C) R,S 14. (A) P, (B) Q,S (C) R

15. 6 16. 1 17. 2

18. 0 19. 1