Department of Chemistry, IIT Bombay

CH 105: Organic Chemistry

End-Semester Examination
Marks: 25 Time: 2 hours September 15, 2018

All answers must be written using blue/black pen. Answers written with pencil will not be corrected.

1. Classify the following compounds as aromatic/antiaromatic/non-aromatic. (2 marks)

a) b)

2. Identify and draw the orbital interactions responsible for driving the equilibrium towards conformer-B.
(1 marks)

3. The molecule given below is a substituted cubane.

a) How many stereoisomers exist for this molecule?
b) How many pairs of enantiomers are possible? (2 marks)

4. Provide an arrow-pushing mechanism for the formation of the products in the following reactions.
(3+2 marks)
a)

b)

5. Draw the Newman projection of the most stable conformers of

a) 2-methylpentane
b) 3-methylpentane
and calculate the energy difference between them. (2 marks)

1
6. Using CIP rules assign priorities to the groups attached to the carbon marked 1 in the following molecule
and then identify the absolute configuration (R/S). (2 marks)

7. Shown below is the structure of an antibiotic nonactin, which is optically inactive. When completely
hydrolyzed, it yields a racemic mixture of nonactic acid. Draw the stereochemical structure of nonactin
from this information using appropriate wedges/dashes at the chiral centres. (2 marks)

nonactin

8. The reaction given below passes through a six-membered chair-like transition state (TS) involving
breaking and formation of sigma bonds. The reaction can be visualized as a combination of two allyl ions.
Draw the MOs involved in the TS. (3 marks)

9. Write the most stable conformers of the following molecules A and B. Calculate the gauche interactions
in each and find the difference in their energy. (3 marks)

10. The reaction given below is an example of syn elimination for the synthesis of olefin.

Identify the products A and B with correct absolute stereochemistry (R/S or E/Z) in the following reaction.
Rationalize the outcome using appropriate conformations with wedge structures. (3 marks)