W03 problems8b

W03 problems8b - a NH 2 O O O Na b O Cl Cl O MeOH(excess O...

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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)
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Unformatted text preview: a) NH 2 O O O Na b) O Cl Cl O MeOH (excess) O O O O O O O Cl O MeO OMe O Na Cl Ph Ph O O NH 3 (excess) Na OMe Li O O O OCH 3 O O COOH O HOOC OH CO 2 H OH HO O O HO CO 2 H OH TA: Danny Ng 3/3/2003 Problem Set 8 c) d) e) 4. Provide the reagents or products for the following reactions. a) 1. excess 2. H 3 O + b) c) 1. NaOH 2. H 3 O + 1. SOCl 2 2. Ph 2 CuLi d) e) 1. SOCl 2 (2 eq.) 2. (CH 3 ) 2 CuLi (excess) 3. PhMgBr (excess) 4. H 3 O + CN O O H 2 SO 4 COOH OH O OH TA: Danny Ng 3/3/2003 Problem Set 8 5. Provide the mechanism for the following reactions. a) b) Reagents (i) Reagents = H 2 O, H 2 SO 4 (ii) Reagents = NaOH (step 1), H 3 O + (step 2) H 2 O...
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This note was uploaded on 04/05/2008 for the course CHEM 30B taught by Professor Rubin during the Winter '05 term at UCLA.

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W03 problems8b - a NH 2 O O O Na b O Cl Cl O MeOH(excess O...

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