Download OU M.Pharma Ph.Chemistry 1st Sem 2019 13151 PCI Advanced Organic Chemistry I Question Paper

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Code No. 13151/ PCI

FACULTY OF PHARMACY

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M. Pharmacy (Pharmaceutical Chemistry) | — Semester (PCl) (Main & Backlog) Examination, January 2019

Subject : Advanced Organic Chemistry - |

Time : 3 hrs Max. Marks : 75

Note : Answer any FIVE questions. All questions carry equal marks.

1. 1. What are the commonly used methods for determining the mechanisms of a reaction? Explain with suitable examples.

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   2. Explain the stability of carbocations and carbanions. 7+8
2. Discuss the mechanism and synthetic applications of any three of the following named reactions.
   1. Ullmann cpling reaction
   2. Dieckmann reaction
   3. Sharpless asymmetric epoxidation

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   4. Michael addition reaction
   5. Baeyer-Villiger oxidation 3x5=15
3. 1. Explain the role of protection in organic synthesis. Explain how hydroxyl grp (1, 2- and 1, 3-diols), carboxyl grp are protected and deprotected in organic synthesis. 6
   2. Write the method of preparation, mechanism and applications of any three of the following synthetic reagents.
      1. N-bromosucinamide

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      2. Dicyclohexyl carbodiimide
      3. Diethyl azodicarboxylate
      4. Aluminium isopropoxide 3x3=9

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4. Discuss the mechanism and stereochemistry of SN¹ and SN² reactions. Explain neighbring grp participation in such reactions. 15
5. 1. Discuss the advantages and important guidelines for disconnection of simple molecules in retrosynthesis.
   2. Explain 1, 2-, 1, 3-, 1, 4- and"1, 5- difunctionalized disconnections with suitable examples. 7+8
6. 1. Mention the heterocyclic nucleus present and also the synthesis of following drugs (any three)
      1. Metronidazole

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      2. Celecoxib
      3. Promazine
      4. Triamterene 3x3=9
   2. Discuss Saytzeff and Hoffman rules of elimination. 6

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7. Write a note on (any three)
   1. Pinner pyrimidine synthesis
   2. Smiles rearrangement
   3. Wilkinson reagent
   4. BOP reagent 3x5=15

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8. 1. Write the steps involved in the synthesis and important use(s) of following drugs :
      1. Ketoconazole
      2. Alprazolam
      3. Mercaptopurine 3x3=9

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   2. Discuss the strategies for synthesis of five and six membered rings thrgh disconnection approach. 6

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