SIKKIM UNIVERSITY

Department of Chemical Sciences

Organic Chemistry
Unit-1: March, 2018
Teacher: Dr. B. G. Roy

Full Marks: 25 Time: 1 hour

Answer Section A and any three questions from Section B.
Section A
1. Write appropriate reagents and products with appropriate stereochemistry to complete the
following reaction. Give mechanism in each case. 10

i)

ii)

Section B
Answer any three (3x5=15)
2. a) 2,4-dinitrofulorobenzene is used for N-terminal amino acid protection during peptide
synthesis. Why 2,4-dinitrofulorobenzene is not used. 2.5
b) Fmoc is another popular amine/hydroxyl protecting group. Discuss its introduction and
removal method from amine. Why it is very special protecting group and what is its
advantage? 2.5

Fmoc

3. a) Give an example of photo-removable protecting group. Discuss about its introduction and
removal on hydroxyl or amine moiety. What are the advantages of photo removable
protecting groups? 2.5
b) How will you carry out following oxidation of alcohols? Give mechanism in each case.
2.5

4. a) Give step by step mechanism for formation of following products? Give reason for specific
stereochemistry of the products. 2.5
 b) Write mechanism for following transformation. Categorize which pericyclic reactions
involved in each step. 2.5

5.