Dolbier HW Solutions 444

Dolbier HW Solutions 444 - O Benzoyl chloride CH 3 CH 2 OH...

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538 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION ( d ) Acyl transfer from benzoyl chloride to the nitrogen of methylamine yields the amide N -methyl- benzamide. ( e ) In analogy with part ( d ), an amide is formed. In this case the product has two methyl groups on nitrogen. ( f ) Acyl chlorides undergo hydrolysis on reaction with water. The product is a carboxylic acid. 20.4 ( b ) Nucleophilic addition of benzoic acid to benzoyl chloride gives the tetrahedral intermediate shown. Dissociation of the tetrahedral intermediate occurs by loss of chloride and of the proton on the oxygen. ( c ) Ethanol is the nucleophile that adds to the carbonyl group of benzoyl chloride to form the tetrahedral intermediate. 1 C 6 H 5 CCl
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Unformatted text preview: O Benzoyl chloride CH 3 CH 2 OH Ethanol Tetrahedral intermediate C 6 H 5 COCH 2 CH 3 OH Cl 1 C 6 H 5 COCC 6 H 5 O O Benzoic anhydride HCl Hydrogen chloride Tetrahedral intermediate C 6 H 5 COCC 6 H 5 O H Cl O 1 C 6 H 5 CCl O Benzoyl chloride C 6 H 5 COH O Benzoic acid C 6 H 5 COCC 6 H 5 HO Cl O Tetrahedral intermediate 1 C 6 H 5 CCl O Benzoyl chloride H 2 O Water 1 C 6 H 5 COH O Benzoic acid HCl Hydrogen chloride 1 C 6 H 5 CCl O Benzoyl chloride 2(CH 3 ) 2 NH Dimethylamine 1 C 6 H 5 CN(CH 3 ) 2 O N , N-Dimethylbenzamide (CH 3 ) 2 NH 2 Cl 2 1 1 C 6 H 5 CCl O Benzoyl chloride 2CH 3 NH 2 Methylamine 1 C 6 H 5 CNHCH 3 O N-Methylbenzamide 1 CH 3 NH 3 Cl 2...
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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