University of Pune 2010 B.Pharm 2.4 : Pharmaceutical Organic Chemistry – II(2008 ) - Question Paper

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Second Year B.Pharmacy Examination, 2010
2.4 : Pharmaceutical Organic Chemistry – II(2008 Course)
Time : three Hours Max. Marks : 80

Instructions :
1) All ques. are compulsory.
2) Answers to the 2 parts should be written in separate books.
3) Neat diagram must be drawn wherever necessary.
4) Black figures to the right indicate full marks.

part – I
1. provide reaction, mechanism and application of any 2 rearrangement of electron deficient carbon atom. 10
OR
1. discuss any 2 nucleophilic rearrangement of electron deficient Nitrogen atom. 10

2. ans the subsequent (any five) : 15
a)What is Mutarotation ? provide its significance.
b)What are configurational and conformational isomers ? Write in brief about Atropisomerism.
c)How will you distinguish ranging from glucose and fructose and glucose and sucrose ?
d)What are amino acids ? explain any 3 methods of synthesis of amino acids.  
e) Draw the Newmann projection formulae of n-butane and explain the energy profile diagram of conformations in n-butane.
f) explain the constitution of Lactose.
g) Synthesize phenylalanine by Strecker's synthesis.

3. ans the subsequent (any three) : 15
a)What are carbohydrates ? Draw the structure of glucose. What will happen when glucose treated with
i) Nitri acid ; ii) Bromine water ;
iii) Sodium borohydrate ?
b)What are proteins ? explain in brief about structure of protein.
c)What is racemic modification ? Enlist the various methods for resolution of racemic mixture. explain in brief about Diastereomer formation method in brief :
d)Write a short note on combinatorial chemistry.
e) explain stereoselective and stereospecific reaction with suitable examples.

part – II
4.
a) explain Fischer-indole and Skraup quinoline synthesis method. 6
b) Write in brief about electrophilic substitution reactions of 5 membered monoheterocyclic ring system. 4
OR
4. provide the methods of synthesis and reactions of the subsequent : 10
i) Thiazole
ii) Isoquinoline

5. ans the subsequent (any five) : 15
a) provide the structure and numbering of
i) Quinoline ii) Benzimidazole iii) Oxazole
b) discuss why pyridine is less reactive than benzene.
c)Discuss chair, boat and twist boat conformation of cyclohexane molecule.
d)Why pyridine undergose electrophilic substitution at ß-position ?
e) provide the reaction and mechanism of Knorr-pyrrole synthesis.
f) Classify rearrangement reactions.
g)What is reterosynthesis ? provide the reterosynthesis of Losrtan.

6. Write short note on (any three) : 15
a) Fries rearrangement
b) Curties rearrangement
c) Hoffman rearrangement
d) Willgerodt reaction
e) Lossen rearrangement.

Earning:   Approval pending.