Dolbier HW Solutions 424

Dolbier HW Solutions 424 - 2 CO 2 H Aminoacetic acid...

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The reaction scheme which may be used is ( g ) Carboxylic acids are halogenated at their a -carbon atom by the Hell Volhard Zelinsky reaction. A catalytic amount of PCl 3 may be used in place of phosphorus in the reaction. ( h ) Dehydrohalogenation of 2-bromobutanoic acid gives 2-butenoic acid. 19.21 ( a ) The compound to be prepared is glycine, an a -amino acid. The amino functional group can be introduced by a nucleophilic substitution reaction on an a -halo acid, which is available by way of the Hell Volhard Zelinsky reaction. ( b ) Phenoxyacetic acid is used as a fungicide. It can be prepared by a nucleophilic substitution using sodium phenoxide and bromoacetic acid. BrCH 2 CO 2 H Bromoacetic acid 1 NaCl C 6 H 5 OCH 2 CO 2 H Phenoxyacetic acid 1. C 6 H 5 ONa 2. H 1 H 2 NCH
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Unformatted text preview: 2 CO 2 H Aminoacetic acid (glycine) NH 3 , H 2 O BrCH 2 CO 2 H Bromoacetic acid CH 3 CO 2 H Acetic acid Br 2 P 1. KOC(CH 3 ) 3 DMSO 2. H 1 CH 3 CH 2 CHCO 2 H Br 2-Bromobutanoic acid CH 3 CH CHCO 2 H 2-Butenoic acid Br 2 P CH 3 CH 2 CH 2 CO 2 H Butanoic acid CH 3 CH 2 CHCO 2 H Br 2-Bromobutanoic acid 1. diethyl ether 2. H 3 O 1 Butylmagnesium chloride CH 3 CH 2 CH 2 CH 2 MgCl 1 Butanal [from part ( b )] CH 3 CH 2 CH 2 CH O 4-Octanol CH 3 CH 2 CH 2 CHCH 2 CH 2 CH 2 CH 3 OH 4-Octanone CH 3 CH 2 CH 2 CCH 2 CH 2 CH 2 CH 3 O H 2 CrO 4 CH 3 CH 2 CH 2 CH 2 Cl 1-Chlorobutane [from part ( c )] CH 3 CH 2 CH 2 CH 2 MgCl Butylmagnesium chloride Mg 518 CARBOXYLIC ACIDS __ __ __...
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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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