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What are Atropisomerism? What is buttressing effect? Write the EXAMINATION – JUNE 2019
MASTER OF SCIENCE (M.Sc. Chemistry)
stereochemistry of Biphenyls
Final Year - Semester-IV 4M.Sc. 4
(Physical Chemistry)
Stereo Chemistry
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Time : 3 Hours Max Marks : 70
Min. Marks : 25
Note : Question 1 is compulsory. Q. 2 to 6 carries equal marks.

Q.1. Write the correct answer :- −

(A) Which of the following compound is optically active –
O
O
(i) ii) (iii) (iv) O
O
(B) Addition of Br2 to Cis-2-butene yields –
(i) Meso 2, 3 dibromobutane
(ii) Racemic 2, 3 dibromobutane
(iii) d-2, 3 dibromo butane
(iv) l – 2, 3 dibromo butane

(C) Measurement of optical rotation as a function of wave length is known

as –
(i) CD (ii) ORD (iii) Cotton Effect (iv) Octant Rule

(D) Write the correct order of the stability of different conformation of

cyclohexane –
(i) Chair form > Half chair form > boat form > Twist boat
(ii) Boat form> Twist boat> Chair form > Half chair form
(iii) Chair form > Twist boat > boat form> Half chair form
(iv) Twist boat > boat form> Chair form > Half chair form

(E) Which of the following Compounds have no chiral axis –

(i) Allenes (ii) Biphenyls
(iii) Spiranes (iv) Chiral Ferrocene

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Q.2. (a) Is the structure shown chiral ? Is it asymmetric? OR
(a) What is enantioselective synthesis? Write the enantioselective synthesis
in a chiral approach of reaction with Hydride donor and Hydroboration.
(b) Write notes on: (any one)
(b) Write details about the molecules with chiral axis and chiral planes. (i) Sharpless epoxidation
(c) Write Notes on: (ii) Diels Alder selective synthesis
(i) Optical Activity
(ii) Non-Carbon Chiral Centres Q.4. (a) What is conformation ? What is butane-gauch interaction? Write the
conformation of n-butane
OR
(b) What do you mean by inversion of chair form of cyclohexane?
(a) “All Assymmetric molecules are dissymmetric but the reverse is not What are the possible pathways through which such an inversion
true.” – Explain. Possible?
(b) What do you mean by the term homotopic, enantiotopic and (c) Draw the stable conformation of the following compounds:
diastreotopic. Explain giving suitable examples. (i) Cis-1,3 tert-butyl cyclohexane
(c) Designate R/S of the following compounds – (any four) (ii) Trans-1,4 di tertiary butyl cyclohexane.
O
H
CH2OCH2CH3 OR
i) H C CH ii) CH3 H iii) CH
3 C
iv) CH2CH2OCH3
H CH3 CH3 (a) Write down the chair and boat form of cyclohexane and discuss
Ph CMe3 H O
their relative stability.
O Ph NHMe O S
v)
vi) vii) viii)
(b) Write the conformation of disubstituated cyclohexanes.
OH
O
CH3 (c) Write notes on: Curtin-Hammett principle
Me S
Me
Q.5. (a) Write the conformation of cis and trans decalins.
Q.3. (a) What is streoselective and streospecific? (b) Write notes on: ORD & CD
(b) Find the element of symmetry, point group and state which are
OR
optically active of the following molecules – (any four)
(i) C2H4 (ii) CHCl3 (iii) CO2 (iv) Cyclohexane (twist boat form) (a) Explain the following:
(i) Bredt’s rule
Br (ii) Octant rule
v) vi) vii) viii) H H
CH3 C
• (b) How will you determine conformation and configuration?
Cl CH3 CH3
Q.6. (a) What are the necessary and sufficient conditions to be optically active
(c) What is mean by the term optical purity and enantiomeric excess? The
of the following compounds?
pure (+) enantiomer of a compound shows a specific rotation + 80o. X
X
Calculate the % of (_) enantiomer of the same compound in a partially Y
C C
n Y
resolved sample showing a specific rotation of _ 20o. (b) Write the stereochemistry of Allenes and Spiranes.
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