FACULTY OF PHARMACY
M. Pharmacy (Pharmaceutical Chemistry) I Semester (Main Backlog)
Examination, January 2019
Subject Advanced Organic Chemistry I
Time 3 hours Max. Marks 75
Note Answer any FIVE questions. All questions carry equal marks.
1 What are the commonly used methods for determining the mechanisms of a
reaction? Explain with suitable examples.
Explain the stability of carbocations and carbanions. 7+8
2 Discuss the mechanism and synthetic applications of any three of the following
named reactions.
Ullmann coupling reaction Dieckmann reaction
Sharpless asymmetric epoxidation Michael addition reaction
Baeyer-Villiger oxidation 3 x 5 15
3 Explain the role of protection in organic synthesis. Explain how hydroxyl group
and 3-diols), carboxyl group are protected and deprotected in organic
synthesis. 6
Write the method of preparation, mechanism and applications of any three of the
following synthetic reagents.
N-bromosucinamide ii) Dicyclohexyl carbodiimide
iii) Diethyl azodicarboxylate iv) Aluminium isopropoxide 3 x 3 9
4 Discuss the mechanism and stereochemistry of SN1 and SN2 reactions. Explain
neighbouring group participation in such reactions. 15
5 Discuss the advantages and important guidelines for disconnection of simple
molecules in retrosynthesis.
Explain and difunctionalized disconnections with suitable
examples. 7+8
6 Mention the heterocyclic nucleus present and also the synthesis of following
drugs (any three)
Metronidazole ii) Celecoxib
iii) Promazine iv) Triamterene 3 x 3 9
Discuss Saytzeff and Hoffman rules of elimination. 6
7 Write a note on (any three)
Pinner pyrimidine synthesis Smiles rearrangement
Wilkinson reagent BOP reagent 3 x 5 15
8 Write the steps involved in the synthesis and important use(s) of following drugs
Ketoconazole ii) Alprazolam iii) Mercaptopurine 3 x 3 9
Discuss the strategies for synthesis of five and six membered rings through
disconnection approach. 6