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University of Pune 2010 B.Pharm 1.4 : Pharmaceutical Organic Chemistry – I (2008 Pattern) - Question Paper

Monday, 22 April 2013 11:30Web

[3856] – 104
First Year B.Pharmacy Examination, 2010

Time: three Hours Total Marks: 80
Instructions :
1) All ques. are compulsory.
2) ans to the 2 parts should be written in separate books.
3) Black figures to the right indicate full marks.

part – I
A) discuss the mechanism involved in Friedel Craft acylation and nitration of Benzene. 10
B) discuss substitution nucleofilic unimolecular reaction mechanism with stereochemistry with suitable examples.

A) Draw the structure of subsequent compound (any 3) : 3
a) 2, four Hexadione
b) Methyl-2- butnenoate
c) Cyclopropane carboxilic acid
d) 3-Methyl-4-pentene-2-one.
B) ans the subsequent (any four) : 12
1) describe and illustrate Tautamerism.

2) Compare the stability of primary, secondary and tertiary, carbonium ion.
3) What is Inductive effect and discuss it with suitable example.
4) What is difference ranging from nucleophilicity and basisity ?
5) Draw as much resonance structure as you can for subsequent
a) Anilline
b) Acetic acid.
6) discuss Huckels rule for aromaticity with suitable example.

3. ans the subsequent (any three) : 15
1) What is resonance ? discuss the rules of resonance with suitable example.
2) Compare SN1 and SN2 mechanism.
3) Write a synthesis of subsequent compound starting with Benzene and with suitable reagent
a) Para nitro toluene
b) Meta nitro toluene.

4) Write a note on optical isomerism. discuss it with a suitable example.

5) describe the subsequent terms and provide any 2 suitable examples of every
a) Activating group
b) Deactivating group
c) Ortho and para director.
part – II
A) elaborate elimination reactions ? explain the Mechanism, stereochemistry, kinetics and orientation involved in elimination reaction. 10
A) discuss why aldehydes are more reactive than ketone for nucleophilic addition reaction and add a note on addition of hydrogen cynide to aldehyde.

5. ans the subsequent (any five) : 15
1) How will you differentiate the subsequent pair of compounds by simple chemical test ?
a) Pentanal and Pentanone
b) Aniline and Phenol.
2) discuss hydrogenation reaction with C-C multiple bond.
3) Why esters are less reactive towards nucleophile than aldehydes ?
4) organize the subsequent compounds in order of increasing acidity.
a) Acetic acid
b) Chloro acetic acid
c) formic acid.
5) define how primary, secondary and tertiary amines can be separated from
6) discuss Canizarros reaction with mechanism.
7) provide any 2 method of synthesis of carboxylic acids.

6. Write note on (any 3) : 15
1) Preparation of Sulphonic acid.
2) Reaction of phenols.
3) Ozonolysis.
4) Saytzaffs and Hoffmann elimination.
5) Knovengel condensation.

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