BIRLA INSTITUTE OF TECHNOLOGY & SCIENCE, PILANI – Hyderabad Campus

SECOND SEMESTER 2017-2018

CHEM F 243 Organic Chemistry - II 10th March- 2018
Duration: 90 min Midsem (Closed Book) Max. Marks: 50
Note: Answer all parts of each question together. Write the explanation to the point.

1. (i) Explain the terms chiral non-racemic and chiral racemic. 2

(ii) (S)-Lactic acid [ (H)(OH)C(Me)(CO2H) is produced in the mussel tissues and (R)- form is
present in the milk. Draw their structures in Flying-Wedge by avoiding the position of lowest
priority above or below the plane. 2
(iii) Are there any chiral centers for these molecules (consider to be almost planar)? If so,
assign them with the configurations and comment on the chirality for these molecules. 4

(iv) If this molecule is taken to the polarimeter to measure the optical activity, what will you
observe? Explain you answer with proper reason. 2

Q2. (i) Among these two molecules, where can we find the pseudo-asymmetric center?
Explain your answer with proper drawings (Fischer’s projections) for both. 3

(ii) Write three separate structures for the molecules with molecular formula H2C2XY (X, Y=
halogen, X can be same or different with Y) where the point group satisfies C2v, Cs, and C2h
only. Where can you find an inversion center of symmetry? 4
(iii) The molecule C3F2Cl2 can exist in both optically active and inactive form. Write one
example for both by mentioning the point group in each case. Show the symmetry elements
by drawing their structures in a Fisher like projections wherever possible. 3
Q3. (i) “Allenes show atropisomerism” True/false: Justify. 2 PTO
(ii) Which spirane among the followings are chiral. Explain your answer. 3

(iii) Comment on the chirality of these molecules. Assign absolute configuration for them
with proper drawings. 3

(iv) Write the structure for the corresponding compound after S 4 operation of the following. 2

Q4. (i) Comment on the optical activity of these molecules by drawing the proper strutures.6

(ii) There were cis/trans isomers for an olefinic compound. One needs to apply heat to
convert trans to cis isomer. Rotational barrier for a double bond is generally higher. Find two
pathways where these barriers can be reduced. 3

(iii) Which one will have more rotational barrier between MeO-N=N-OMe and Me-N=N-Me? 1

Q4. (i) The concept of different conformational isomers can be identified through IR-
spectrum analysis of meso and dl-pair of Me-C(H)(NH2)-C(H)(NH2)-Me. Draw the proper
Newman’s projections to justify this statement. 4
(ii) Hydrogen peroxide can possibly be found with three different conformational isomers
with different ratio. Find them with possible ratios. 3+1
(iv) Explain the term s-cis and s-trans isomers of a molecule with examples. 2

End