M.Sc.
-I (Chemistry) (CBCS Pattern) Semester - II
PSCCHT06 - Organic Chemistry
P. Pages : 3 GUG/S/23/11229
*1407*
Time : Three Hours Max. Marks : 80
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Notes : 1. All questions are compulsory and carry equal marks.
1. a) Explain the following reactions with mechanisms. 8
i) Claisen rearrangement reaction
ii) Birch reduction
b) 1) Use suitable organometallic reagent in following reaction 8
[CH3MgBr / Cu − Br2 , (C2H5 )2 Zn , (H3C − Li)]
Me
?
i)
H2O/H+
Br Br OH
?
ii) R − C = C − CHO R − C = C − C − C 2 H5
H2O/H+
H H H
OH
?
iii) R − C = C − C − CH3 R − C = C − C − CH 3
H H2O/H+
H H H CH3
CH3
? OH
iv) H2O/H +
2) Explain Knoevengel condensation with mechanism.
OR
c) Write a note on 4
i) Hydrolysis of esters ii) Ammonolysis of esters.
d) Explain the term electrophile and nucleophile? Give the mechanism and stereochemistry 4
of addition reaction involving nucleophiles.
e) Define chemo selectivity. Give the mechanism of hydrogenation of double and triple bonds. 4
f) Write the note on metal hydride reduction of unsaturated carbonyl compounds with suitable 4
example.
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2. a) Explain the following rearrangement reaction with mechanisms. 8
i) Wagner-Meerwein rearrangement.
ii) Pinacol-Pinacolone rearrangement.
b) Explain type of free radicals. Discuss free radical substitution mechanism at an aromatic 8
and aliphatic substrate.
OR
c) Write a note on 4
i) Hoffman rearrangement
d) Discuss the reactivity of neighbouring group participation for aliphatic and aromatic 4
substrate.
e) What is the effect of solvent on the reactivity of free radical substitution? 4
f) Explain following rearrangement. 4
i) Lossen rearrangement
ii) Beckman rearrangement
3. a) Discuss the following terms. 8
i) Auto-oxidation
ii) Hunsdiecker reaction
b) Explain the Saytzeff’s and Hoffman’s rules in elimination reaction. 8
OR
c) Explain : 4
i) Fenton’s reagent
ii) Chlorosulphonation reaction
d) Give the mechanism of E1 reaction. 4
e) Explain the effect of solvent and leaving group on E 2 elimination reaction. 4
f) Write short note on Sandmeyer reaction. 4
4. a) Explain the principle of green chemistry. 8
b) Discuss the following reaction. 8
i) Biginelli reaction
ii) Passeneno reaction
OR
c) Write short note on; 4
i) Sono chemistry
ii) Microwave induced reaction
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d) Give green Synthesis of 4
i) Paracetamol from phenol
ii) Ibuprofen
e) What is Nano chemistry? Explain nanotubes and nanorods. 4
f) Explain the following reaction with example 4
i) Photochemical reaction
ii) Rearrangement reaction
5. a) Explain the hydrogenation of alkene. 2
b) Write Mannich reaction. 2
c) Explain Schmidt rearrangement. 2
d) Write a note on neighbouring group assistance of free radical reactions. 2
e) Explain free radical rearrangement. 2
f) What is E 2 elimination reaction. 2
g) Explain solvent free reaction with example. 2
h) Discuss the choice of solvent in green chemistry. 2
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