W03 problems8b key

W03 problems8b key - TA: Danny Ng 3/3/2003 Problem Set 8...

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OCH 3 O Cl O N H O CH 3 O O O CH 3 Problem Set 8 (Chapter 18 Carboxylic Acid Derivatives) TA: Danny Ng 3/3/2003 2. Rank the following carboxylic acid derivatives according to their relative reactivity. (1 = most reactive, 4 = least reactive) 1. Provide the structures for the following compounds. Pay attention to stereochemistry if applicable. a) cis -1,4-dicyanocyclohexane b) benzoyl heptanoyl anhydride c) 3 R -methoxy-hexanoyl chloride d) isopropyl pentanoate e) N,N -dipropyl-butanoylamide f) 2 S -ethyl-hexanoylnitrile 3. Predict the products for the following interconversions between carboxylic acid derivatives. If no reaction is expected, write NR. (Hint: keep in mind the relative reactivity of carboxylic acid derivatives) a) NH 2 O O O Na b) O Cl Cl O MeOH (excess) CN NC O O O Cl O OMe O O N O CN 1 2 3 4 NR (amide is the least reactive derivative, can’t be converted to a more reactive one.) O MeO OMe O (acyl chloride is converted to less reactive ester)
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O O O O O O O Cl O MeO OMe O
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W03 problems8b key - TA: Danny Ng 3/3/2003 Problem Set 8...

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