University Of Pune Question Paper
First Year B.Pharmacy Examination, 2010
1.4 : PHARMACEUTICAL ORGANIC CHEMISTRY – I
(2008 Pattern)
Time: 3 Hours Total Marks: 80
Instructions : 1) All questions are compulsory.
2) Answer to the two Sections should be written in separate
books.
3) Black figures to the right indicate full marks.
SECTION – I
1. A) Explain the mechanism involved in Friedel Craft acylation and nitration of
Benzene. 10
OR
B) Explain substitution nucleofilic unimolecular reaction mechanism with
stereochemistry with suitable examples.
2. A) Draw the structure of following compound (any 3) : 3
a) 2, 4 Hexadione
b) Methyl-2- butnenoate
c) Cyclopropane carboxilic acid
d) 3-Methyl-4-pentene-2-one.
B) Answer the following (any four) : 12
1) Define and illustrate Tautamerism.
2) Compare the stability of primary, secondary and tertiary, carbonium ion.
3) What is Inductive effect and explain it with suitable example.
4) What is difference between nucleophilicity and basisity ?
5) Draw as much resonance structure as you can for following
a) Anilline
b) Acetic acid.
6) Explain Huckels rule for aromaticity with suitable example.
3. Answer the following (any three) : 15
1) What is resonance ? Explain the rules of resonance with suitable example.
2) Compare SN1 and SN2 mechanism.
3) Write a synthesis of following compound starting with Benzene and with
suitable reagent
a) Para nitro toluene
b) Meta nitro toluene.
4) Write a note on optical isomerism. Explain it with a suitable example.
5) Define the following terms and give any two suitable examples of each
a) Activating group
b) Deactivating group
c) Ortho and para director.
SECTION – II
4. A) What are elimination reactions ? Discuss the Mechanism, stereochemistry,
kinetics and orientation involved in elimination reaction. 10
OR
A) Explain why aldehydes are more reactive than ketone for nucleophilic addition
reaction and add a note on addition of hydrogen cynide to aldehyde.
5. Answer the following (any five) : 15
1) How will you differentiate the following pair of compounds by simple chemical
test ?
a) Pentanal and Pentanone
b) Aniline and Phenol.
2) Explain hydrogenation reaction with C-C multiple bond.
3) Why esters are less reactive towards nucleophile than aldehydes ?
4) Arrange the following compounds in order of increasing acidity.
a) Acetic acid
b) Chloro acetic acid
c) formic acid.
5) Describe how primary, secondary and tertiary amines can be separated from
mixture.
6) Explain Canizarros reaction with mechanism.
7) Give any two 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.
——————
First Year B.Pharmacy Examination, 2010
1.4 : PHARMACEUTICAL ORGANIC CHEMISTRY – I
(2008 Pattern)
Time: 3 Hours Total Marks: 80
Instructions : 1) All questions are compulsory.
2) Answer to the two Sections should be written in separate
books.
3) Black figures to the right indicate full marks.
SECTION – I
1. A) Explain the mechanism involved in Friedel Craft acylation and nitration of
Benzene. 10
OR
B) Explain substitution nucleofilic unimolecular reaction mechanism with
stereochemistry with suitable examples.
2. A) Draw the structure of following compound (any 3) : 3
a) 2, 4 Hexadione
b) Methyl-2- butnenoate
c) Cyclopropane carboxilic acid
d) 3-Methyl-4-pentene-2-one.
B) Answer the following (any four) : 12
1) Define and illustrate Tautamerism.
2) Compare the stability of primary, secondary and tertiary, carbonium ion.
3) What is Inductive effect and explain it with suitable example.
4) What is difference between nucleophilicity and basisity ?
5) Draw as much resonance structure as you can for following
a) Anilline
b) Acetic acid.
6) Explain Huckels rule for aromaticity with suitable example.
3. Answer the following (any three) : 15
1) What is resonance ? Explain the rules of resonance with suitable example.
2) Compare SN1 and SN2 mechanism.
3) Write a synthesis of following compound starting with Benzene and with
suitable reagent
a) Para nitro toluene
b) Meta nitro toluene.
4) Write a note on optical isomerism. Explain it with a suitable example.
5) Define the following terms and give any two suitable examples of each
a) Activating group
b) Deactivating group
c) Ortho and para director.
SECTION – II
4. A) What are elimination reactions ? Discuss the Mechanism, stereochemistry,
kinetics and orientation involved in elimination reaction. 10
OR
A) Explain why aldehydes are more reactive than ketone for nucleophilic addition
reaction and add a note on addition of hydrogen cynide to aldehyde.
5. Answer the following (any five) : 15
1) How will you differentiate the following pair of compounds by simple chemical
test ?
a) Pentanal and Pentanone
b) Aniline and Phenol.
2) Explain hydrogenation reaction with C-C multiple bond.
3) Why esters are less reactive towards nucleophile than aldehydes ?
4) Arrange the following compounds in order of increasing acidity.
a) Acetic acid
b) Chloro acetic acid
c) formic acid.
5) Describe how primary, secondary and tertiary amines can be separated from
mixture.
6) Explain Canizarros reaction with mechanism.
7) Give any two 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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