Homework%207 - Homework 7 Fall 2009 These problems should...

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Homework 7 Fall 2009 These problems should be finished before next Wednesday or Friday the latest. Second part of it will be possible after Friday lecture. 1. Question from the MCAT test: O A O OMe OH methyl salicylate OH OH salicylic acid B O O OH C O H 3 C 1. How do you convert salicylic acid to aspirin? 2. How do you convert methyl salicylate to salicylic acid? 3. How do you convert salicylic acid to methyl salicylate? 4. Which one of these three compounds will dissolve in sodium bicarbonate? 2. Write the structures of formic acid, malonic acid, acetic acid, gamma-aminobutyric acid. 3. Show the best way for the following transformations: O OH Ph OH OH Br O H O H OH 4 . Propose reasonable mechanism for the following transformations:
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NO 2 OH O O HO - NO 2 O OH O O O OH H + O O 5. Write structures of intermediates A and B and final product C . Draw clear mechanism from A to B and B to C . O O O H + /H 2 O A B C enol heat 6. Ascorbic acid (vitamin C) is not a carboxylic acid and yet has a pKa of 4.2. Show the acidic proton. Explain
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