University Of Pune Question Paper
Second Year B.Pharmacy Examination, 2010
2.4 : PHARMACEUTICAL ORGANIC CHEMISTRY – II
(2008 Course)
Time : 3 Hours Max. Marks : 80
Instructions :1) All questions are compulsory.
2) Answers to the two Sections should be written in separate
books.
3) Neat diagram must be drawn wherever necessary.
4) Black figures to the right indicate full marks.
SECTION – I
1. Give reaction, mechanism and application of any two rearrangement of electron
deficient carbon atom. 10
OR
1. Explain any two nucleophilic rearrangement of electron deficient Nitrogen atom. 10
2. Answer the following (any five) : 15
a) What is Mutarotation ? Give its significance.
b) What are configurational and conformational isomers ? Write in brief about
Atropisomerism.
c) How will you distinguish between glucose and fructose and glucose and
sucrose ?
d) What are amino acids ? Discuss any three methods of synthesis of amino
acids.
e) Draw the Newmann projection formulae of n-butane and discuss the energy
profile diagram of conformations in n-butane.
f) Discuss the constitution of Lactose.
g) Synthesize phenylalanine by Strecker’s synthesis.
3. Answer the following (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 ? Discuss in brief about structure of protein.
c) What is racemic modification ? Enlist the different methods for resolution of
racemic mixture.
Discuss in brief about Diastereomer formation method in brief :
d) Write a short note on combinatorial chemistry.
e) Discuss stereoselective and stereospecific reaction with suitable examples.
SECTION – II
4. a) Discuss Fischer-indole and Skraup quinoline synthesis method. 6
b) Write in brief about electrophilic substitution reactions of five membered
monoheterocyclic ring system. 4
OR
4. Give the methods of synthesis and reactions of the following : 10
i) Thiazole
ii) Isoquinoline
5.Answer the following (any five) : 15
a) Give the structure and numbering of
i) Quinoline ii) Benzimidazole iii) Oxazole
b) Explain 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 β-position ?
e) Give the reaction and mechanism of Knorr-pyrrole synthesis.
f) Classify rearrangement reactions.
g) What is reterosynthesis ? Give 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.
Second Year B.Pharmacy Examination, 2010
2.4 : PHARMACEUTICAL ORGANIC CHEMISTRY – II
(2008 Course)
Time : 3 Hours Max. Marks : 80
Instructions :1) All questions are compulsory.
2) Answers to the two Sections should be written in separate
books.
3) Neat diagram must be drawn wherever necessary.
4) Black figures to the right indicate full marks.
SECTION – I
1. Give reaction, mechanism and application of any two rearrangement of electron
deficient carbon atom. 10
OR
1. Explain any two nucleophilic rearrangement of electron deficient Nitrogen atom. 10
2. Answer the following (any five) : 15
a) What is Mutarotation ? Give its significance.
b) What are configurational and conformational isomers ? Write in brief about
Atropisomerism.
c) How will you distinguish between glucose and fructose and glucose and
sucrose ?
d) What are amino acids ? Discuss any three methods of synthesis of amino
acids.
e) Draw the Newmann projection formulae of n-butane and discuss the energy
profile diagram of conformations in n-butane.
f) Discuss the constitution of Lactose.
g) Synthesize phenylalanine by Strecker’s synthesis.
3. Answer the following (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 ? Discuss in brief about structure of protein.
c) What is racemic modification ? Enlist the different methods for resolution of
racemic mixture.
Discuss in brief about Diastereomer formation method in brief :
d) Write a short note on combinatorial chemistry.
e) Discuss stereoselective and stereospecific reaction with suitable examples.
SECTION – II
4. a) Discuss Fischer-indole and Skraup quinoline synthesis method. 6
b) Write in brief about electrophilic substitution reactions of five membered
monoheterocyclic ring system. 4
OR
4. Give the methods of synthesis and reactions of the following : 10
i) Thiazole
ii) Isoquinoline
5.Answer the following (any five) : 15
a) Give the structure and numbering of
i) Quinoline ii) Benzimidazole iii) Oxazole
b) Explain 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 β-position ?
e) Give the reaction and mechanism of Knorr-pyrrole synthesis.
f) Classify rearrangement reactions.
g) What is reterosynthesis ? Give 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.
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