1
Confidential
In connection with ................M.Sc Semester III............Examination, 2018.... Subject....Chemistry......Paper……
102……..give the copyright of the manuscript to Vidyasagar University. The paper has been set in conformity with
the syllabus.
___________________
Paper Setter
Write the answers to Questions of each/Half/Part/Group in separate books wherever necessary
Year of Examination........ 2018 ...............
Subject................. Chemistry (ORGANIC)............
Paper..... 102 ....../Half/Part/Group.............
Full Marks...... 40 ......Exam. hours........ 2 hours.......
The figures in the margin indicate full marks.
Candidates are required to give their answers in their own words as far as practicable. Illustrate
the answer whenever necessary
Sl.No Questions Marks
1. Answer any four.
a. What is inverse electron demand in Diels-Alder reaction?
b. Illustrate umpolung Diels-Alder reaction with at least two
example.
c. State and explain the term ‘torquoselectivity’
d. Draw the HOMO and LUMO of following system at GS
and ES indicating nodes and symmetry.
i)Allyl cation ii) Allyl anion . iii)
e. How would you explain the acidic reagent can catalyse
cycloaddition reactions?
f. How do you prove that citral is an α-β unsaturated aldehyde.
What is biogenetic isoprene rule?
g.
h.
Define the term Olefin metathesis.
Paper-setter and moderators are requested not to disclose their identities by putting Signature or initials within the question box.
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Paper setter....................................................... Moderator.....................................................
Reference to Text etc.
All paper-setter specially those of literature, Language etc. must give (a) Internal....................................................
Page reference of passage etc. quoted in the questions here under.
(1) (b) External...................................................
(2)
(3)
2
Sl.No Questions Marks
2.
a. Predict product of the following reactions with mechanism. (any four)
b. What are the characteristic feature of pericyclic reactions? State
Woodward-Hoffman rules for electrocyclic ring closure reactions.
c. Citronellal has the molecular formula C10H18O and is a chiral molecule.
Reduction of citronellal gives citronellol C 10H20O and an oxidation gives
citronellic acid C10H18O2. Oxidation of citronellal with chromic acid gives 3-
methyl adepic acid and acetone. What is the probable structure of
citronellal?
d. Give retro synthetic analysis and an efficient synthesis of each of the following
compounds (attempt any four).
OMe
OMe
MeO
O
i) ii) NH
MeO
O
H O
CO2Me CO2Et
O iv)
iii)
CO2Me Ph Ph
H
O
v) O
O
Paper-setter and moderators are requested not to disclose their identities by putting Signature or initials within the question box.
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Paper setter....................................................... Moderator.....................................................
Reference to Text etc.
All paper-setter specially those of literature, Language etc. must give (a) Internal....................................................
Page reference of passage etc. quoted in the questions here under.
(1) (b) External...................................................
(2)
(3)
3
Sl.No Questions Marks
e. Predict the product with plausible mechanism.
PCy3
Et3N Cl Ph
a) CH3CH2OH + DMSO + (COCl)2 b) N
Ru
Cl PCy
Ts 3
OSiR3
Ph3P,DEAD d)
c) HO Grubb 1st
Mei
H
gen cat (4 mole%)
250C 70%
Predict the product with plausible mechanism(attempt any four)
f.
O
H2O2/OH 1NaH
a) b)
TsO 2. MeLi
Ts-NH-NH2 OH
3.TsCl
4.Base
1.NH2OH O
c) d)
HCl
2.AcCl O
e) EtO2C H
+ PhCHO + CO(NH2)2
O
g. Provide a mechanism for the following transformation, including a 3-D structure that
accounts for the selectivity of the chlorination
h. Use both the Diels-Alder and aldol reactions to propose an efficient
synthetic sequence for the preparation of the compound. You may use
compounds of six or less carbons.
Paper-setter and moderators are requested not to disclose their identities by putting Signature or initials within the question box.
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Paper setter....................................................... Moderator.....................................................
Reference to Text etc.
All paper-setter specially those of literature, Language etc. must give (a) Internal....................................................
Page reference of passage etc. quoted in the questions here under.
(1) (b) External...................................................
(2)
(3)
4
5
Sl.No Questions Marks
3.
a. i) Predict the products and identify the stereochemistry of both reactant and
product.
4+4
OTs
t-BuO
OH
Ii) Rationalize the following observation.
Me2N OTs Et3N/EtOH CHO
H2O
Me2N OTs
Et3N/EtOH CHO + Me2N
H2O
11%
alkene mixture
49%
Suggest mechanism for each of the following pericyclic transformations.
b. 4x2
a. b.
c. d.
Paper-setter and moderators are requested not to disclose their identities by putting Signature or initials within the question box.
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Paper setter....................................................... Moderator.....................................................
Reference to Text etc.
All paper-setter specially those of literature, Language etc. must give (a) Internal....................................................
Page reference of passage etc. quoted in the questions here under.
(1) (b) External...................................................
(2)
(3)
6
Sl.No Questions Marks
c. i) If DNA is double stranded, how it can denature to access the 2+2+4
information nucleotide sequence.
ii) Why there is restriction of base pairing Adenine with Thymene or
Guanine with cytosine.
iii) State the main differences between DNA and RNA considering the
structure and biological role
d. i) . Distinguish between nucleotide and nucleoside? 2+4+2
ii) Describe the basic feature of the DNA double helix structure.
iii) What are the similarities between primary nucleic acid structure
and primary protein structure
