Dolbier HW Solutions 464

Dolbier HW Solutions 464 - Ethyl bromoacetate BrCH 2 COCH 2...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
( c ) Ethanol can be converted to ethyl acetate by reaction with acetic acid, acetyl chloride, or acetic anhydride from parts ( a ) and ( b ). or or ( d ) Ethyl bromoacetate is the ethyl ester of bromoacetic acid; thus the f rst task is to prepare the acid. We use the acetic acid prepared in part ( a ), converting it to bromoacetic acid by the Hell Volhard Zelinsky reaction. Alternatively, bromoacetic acid could be converted to the corresponding acyl chloride, then treated with ethanol. It would be incorrect to try to brominate ethyl acetate; the Hell Volhard Zelinsky method requires an acid as starting material, not an ester. ( e ) The alcohol BrCH 2 CH 2 OH, needed in order to prepare 2-bromoethyl acetate, is prepared from ethanol by way of ethylene. Then ( f ) Ethyl cyanoacetate may be prepared from the ethyl bromoacetate obtained in part ( d ). The bromide may be displaced by cyanide in a nucleophilic substitution reaction.
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Ethyl bromoacetate BrCH 2 COCH 2 CH 3 O Ethyl cyanoacetate CCH 2 COCH 2 CH 3 N O NaCN S N 2 BrCH 2 CH 2 OH 2-Bromoethanol 2-Bromoethyl acetate CH 3 COCH 2 CH 2 Br O or CH 3 CCl O CH 3 COCCH 3 O O CH 3 CH 2 OH Ethanol BrCH 2 CH 2 OH 2-Bromoethanol Br 2 H 2 O H 2 SO 4 heat Ethylene CH 2 CH 2 CH 3 CO 2 H Acetic acid BrCH 2 CO 2 H Bromoacetic acid BrCH 2 COCH 2 CH 3 O Ethyl bromoacetate CH 3 CH 2 OH H 1 Br 2 P 1 CH 3 CH 2 OH Ethanol Acetic anhydride O O CH 3 COCCH 3 CH 3 COCH 2 CH 3 O Ethyl acetate pyridine 1 CH 3 CH 2 OH Ethanol Acetyl chloride O CH 3 CCl CH 3 COCH 2 CH 3 O Ethyl acetate pyridine 1 CH 3 CH 2 OH Ethanol Acetic acid O CH 3 COH 1 CH 3 COCH 2 CH 3 O Ethyl acetate Water H 2 O H 1 558 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION...
View Full Document

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.

Ask a homework question - tutors are online