Dolbier HW Solutions 465

Dolbier HW Solutions 465 - O 1 Benzoic anhydride C 6 H 5...

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( g ) Reaction of the acetyl chloride prepared in part ( a ) or the acetic anhydride from part ( b ) with ammonia gives acetamide. ( h ) Methylamine may be prepared from acetamide by a Hofmann rearrangement. ( i ) The desired hydroxy acid is available from hydrolysis of the corresponding cyanohydrin, which may be prepared by reaction of the appropriate aldehyde with cyanide ion. In this synthesis the cyanohydrin is prepared from ethanol by way of acetaldehyde. 20.29 ( a ) Benzoyl chloride is made from benzoic acid. Oxidize toluene to benzoic acid, and then treat with thionyl chloride. ( b ) Benzoyl chloride and benzoic acid, both prepared from toluene in part ( a ), react with each other to give benzoic anhydride. Benzoic acid C 6 H 5 COH O Benzoyl chloride C 6 H 5 CCl
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Unformatted text preview: O 1 Benzoic anhydride C 6 H 5 COCC 6 H 5 O O Benzoic acid Toluene C 6 H 5 CH 3 K 2 Cr 2 O 7 , H 2 SO 4 H 2 O, heat C 6 H 5 COH O Benzoyl chloride C 6 H 5 CCl O SOCl 2 H 2 O, H 1 , heat 2-Hydroxypropanoic acid 2-Hydroxypropanenitrile OH CH 3 CHC N 1. HO 2 , H 2 O, heat 2. H 1 or CH 3 CHCOH OH O CH 3 CH 2 OH O CH 3 CH Acetaldehyde Ethanol PCC CH 2 Cl 2 KCN H 1 2-Hydroxypropanenitrile OH CH 3 CHC N CH 3 CHCOH OH O CH 3 CH O OH CH 3 CHC N Br 2 , HO 2 , H 2 O O CH 3 CNH 2 CH 3 NH 2 Methylamine Acetamide [prepared as in part ( g )] or Acetyl chloride CH 3 CCl O Acetic anhydride CH 3 COCCH 3 O O Acetamide CH 3 CNH 2 O NH 3 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION 559...
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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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