Dolbier HW Solutions 443

Dolbier HW Solutions 443 - 20.3 b Benzoyl chloride reacts...

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CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION 537 ( e ) The ending - amide reveals this to be a compound of the type . ( f ) This compound differs from 2-phenylbutanamide in part ( e ) only in that it bears an ethyl sub- stituent on nitrogen. ( g ) The - nitrile ending signiFes a compound of the type RC > N containing the same number of carbons as the alkane RCH 3 . 20.2 The methyl groups in N , N -dimethylformamide are nonequivalent; one is cis to oxygen, the other is trans. The two methyl groups have different chemical shifts. Rotation about the carbon–nitrogen bond is required to average the environments of the two methyl groups, but this rotation is relatively slow in amides as the result of the double-bond character im- parted to the carbon–nitrogen bond, as shown by these two resonance structures.
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Unformatted text preview: 20.3 ( b ) Benzoyl chloride reacts with benzoic acid to give benzoic anhydride. ( c ) Acyl chlorides react with alcohols to form esters. The organic product is the ethyl ester of benzoic acid, ethyl benzoate. 1 C 6 H 5 CCl O Benzoyl chloride CH 3 CH 2 OH Ethanol 1 C 6 H 5 COCH 2 CH 3 O Ethyl benzoate HCl Hydrogen chloride 1 C 6 H 5 CCl O Benzoyl chloride C 6 H 5 COH O Benzoic acid 1 C 6 H 5 COCC 6 H 5 O O Benzoic anhydride HCl Hydrogen chloride C H O N CH 3 CH 3 1 2 C H O N CH 3 CH 3 2-Phenylbutanenitrile CH 3 CH 2 CHC N C 6 H 5 CH 3 CH 2 CHCNHCH 2 CH 3 O C 6 H 5 N-Ethyl-2-phenylbutanamide CH 3 CH 2 CHCNH 2 O C 6 H 5 2-Phenylbutanamide RCNH 2 O...
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