Damha Org3 - Problem Set1

Damha Org3 - Problem Set1 - Fall 2008 CHEM 302 - PROBLEM...

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CHEM 302 - PROBLEM SET 1 1. Draw all the keto and enol forms of ascorbic acid (vitamin C). Why is the one shown the most stable? Explain why the C-3 OH group of vitamin C is more acidic than the C-2 OH group. 2. The phenols named below have approximately p K a values of 4, 7, 9, 10 and 11. Suggest with explanations which p K a value belongs to which phenol. 2,4-dinitrophenol, 4-nitrophenol, 2,4,5-trimethylphenol, phenol, 2-chlorophenol. 3. Bromination of phenol affords 2,4,6-tribromophenol. So what happens if we force this compound to react again with bromine? Will the reaction then occur in the meta positions? Actually, it is possible to brominate 2,4,6-tribromophenol if we use bromine in acetic acid, but the product is the structure shown below. Account for the formation of the product. OH Br Br Br Br 2 AcOH, NaOAc O Br Br Br Br 2,4,6-tribromophenol This product can be used for bromination as in the monobromination of this amine. Suggest a mechanism and explain the selectivity.
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This note was uploaded on 03/06/2012 for the course CHEM 302 taught by Professor Sleiman during the Winter '12 term at McGill.

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Damha Org3 - Problem Set1 - Fall 2008 CHEM 302 - PROBLEM...

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