Veer Narmad South Gujarat University 2011-2nd Sem M.Sc Chemistry SB-2702 organic : - 2 ( ) ( Regular & Eve.) - Question Paper
SB-2702
M. Sc. (Part - I) (Sem. - II) Examination
March/April - 2011
Organic Chemistry : Paper - II
[Total Marks : 70
Time : 3 Hours]
Instructions :
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Fillup strictly the details of signs on your answer book.
Name of the Examination :
M.Sc. (Part - I) (Sem. - 2)
Name of the Subject:
Organic Chemistry - 2
-Section No. (1,2,.....): NIL
Student's Signature
-Subject Code No.:
(2) Figures to the right indicate full marks of the questions.
(3) Answer written first will be examined.
Give mechanism and a synthetic application of any three of the following :
18
(a) Arndt-Eistert Synthesis
(b) Dakin Reaction
(c) Leukarts Reaction
(d) Michael Reaction
(e) Wittig Reaction.
(a) Discuss SN1 aliphatic nucleophilic substitution reaction 6 mechanism.
OR
(a) Discuss ArSN1 aromatic nucleophilic substitution reaction 6 mechanism.
(b) Discuss nucleophilic substitution reaction of allylic halides. 6
OR
(b) Explain the substitution reaction mechanism of 6
h3c -ch = ch- ch2oh+SOCl2 h3c -ch-ch = ch2+so2
Cl
(100% Yield)
(c) Explain the following sjy2 reaction.
CH=
OH
0
C-c........H Dilute OH c
I - J
Br
(R)-2 - Bromo -propanoic acid
OR
O
0
OH
(R) - Lactate anion
OH
0
CHo /
-C........H
ch3
-c........H
OH
Cone, OH
JC-
0
0
Br
(R)-2 - Bromo -
(R) - Lactate anion
propanoic acid
3 Answer any three of the following : 18
(b) Explain the reaction of 1,3-butadiene (0.03 M) with HBr 6 (0.03 M) gives 1,2-addition product at minus (-) 80C and
1,4-addition product of plus (+) 40C.
(c) Discuss thermodynamic and kinetic controlled reaction of 6 Naphthalene and concentrated H2S04 (d 1.84), a chemical reaction conducted at 80C and at 160C.
(d) Discuss quantitative relationships between molecular 6 structure and chemical reactivity of Hammett equation.
(e) Discuss quantitative relationships between molecular 6 structure and chemical reactivity of Taft equation.
4 Answer any four of the following : 16
(a) Give primary kinetic isotope effect on oxidation reaction 4 of 2-propanol with acidic K2Cr2Or
(b) Discuss and reaction mechanisms involved in 4
solvalysis of 2-bromopropane.
(c) Give hydrolysis of following isomeric allyl chloride (I, II)
C = CHCH2C1 , yC ch=ch2
H.3C7 n&'ki
I II
gives a mixture of 85% tertiary alcohol and 15% primary alcohol.
(d) Discuss Von Richter Rearrangement reaction. 4
(e) Discuss Sommelet-Hauser Rearrangement reaction. 4
(f) Discuss Smiles Rearrangement reaction. 4
SB-2702] 3 [300]
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