Department of Chemistry, IIT Bombay

CH 105:Organic Chemistry
End-Semester Examination
Marks: 25 Time: 2 hours September 13, 2017

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

1. Identify the following pairs as “Identical / Enantiomers / Diastereomers / Constitutional isomers”.

(2 marks)
a. b.

2. Identify the orbital interactions involved in the following rearrangement. (1 marks)

3. Identify the structure of the productofthe following reaction. Explain its formation with the help of
arrow-pushing mechanism. (3 marks)

4. Provide an arrow-pushing mechanism for the formation of the product in the following reaction.
(3 marks)

5. In the following reaction: A. Write the conformation of the starting compound. B. Identify the orbital
interactions involved for ‘*’arrow. C. Identify the stereochemistry and the structure of the major product.
(3 marks)

6. Assign the absolute configurations (R/S) for the following molecules. (2 marks)
a) b)

1
7. Write the most stable conformations of the following molecules. Identify and pictorially show the
symmetry elements present inthatconformer. (4 marks)
a) b)

8. Which of the following bromides will give more stable ionized form in a polar medium such as acetic
acid? (1 mark)

9. Which of the following ketones will have higher dipole moment? (1 mark)

10. Based on the analysis of the highest occupied molecular orbital (HOMO) and the lowest unoccupied
molecular orbital (LUMO) (show picture), identify whether following reaction will take place. Your
answer should be based on the orbital interactions. (3 marks)

11. Match the structures in Column P with the ‘A values’ in Column Q. (2 marks)

  Column P    Column Q (kcal/mol)

1.  a.  0.8 

 
2.  b.  1.8 
 
3.  c.  2.9 
 

4.  d.  4.0