University of Pune 2010 B.Pharm Pharmaceutical Chemistry – II( Organic) (2004 ) - Question Paper

[3856] – 14
First Year B.Pharm. Examination, 2010

Instructions :
1) ques. No. one and five are compulsory. Out of the remaining attempt two ques. from part I and two ques. from part II.
2) Answers to the 2 parts should be written in separate books.
3) Black figures to the right indicate full marks.
Time : three Hours Max. Marks : 80

part – I
1.
A) describe any 4 of the subsequent : (4)
1) Carbocation
2) Stereochemistry
3) Inductive effect
4) Nucleophile
5) Tautomerism.
B) Draw the structures of subsequent compounds (any four) : (4)
1) two amino benzonitrile.
2) Cyclohexane 1, 4, dicarboxylic acid.
3) Naphthalene 1, eight disulfonic acid.
4) 1, 3, five trichloro benzene.
5) 2, 2, dichloropropionic acid.
C) What do you mean by Geometrical isomerism ? (2)

2. provide reasons (any 5) : (15)
i) Ammonia is a stronger base over aniline.
ii) p-nitrophenol is a stronger acid than phenol.
iii) Halogens though deactivators are O, P, directors in electrophilic aromatic substitution.
iv) Aldehydes are more reactive than ketones.
v) Guanidine is 1 of the strongest organic base.
vi) Nitro benzene when reacted with Nitrating mixture provide m-dinitrobenzene.

3.
a) discuss electrophilic aromatic substitution with respect to Nitration and halogenation. (5)
b) discuss Electrophilic aromatic substitution in Napthalene. (5)
c) discuss SN1 reaction. (5)

4. Write short notes on (any three) : (15)
i) Enantiomerism
ii) SN2 reaction
iii) Friedal Craft Alkylation
iv) Orientation in monosubstituted benzene.

part – II
5. describe elimination reaction. discuss E1 and E 1cb reactions in detail. (10)

6.
a) discuss addition reactions across C = O bond. (7)
b) Compare and contrast elimination and substitution reactions. (8) -3- [3856] – 14

7.
a) discuss preparation of carboxylic acid derivatives. (5)
b) discuss cannizaro reaction with examples. (5)
c) discuss reactions of carboxylic acids. (5)

8. Starting from benzene or toulene and suitable reagents how will you synthesize the subsequent (give only reaction equations and reaction conditions.) Solve any 5 of subsequent : (15)
1) Anthranilic acid
2) P. nitro acetanilide
3) M-nitro benzoic acid
4) 2, 4, six trinitrophenol
5) P-aminophenol
6) Diphenyl ether.

Earning:   Approval pending.