Dolbier HW Solutions 423

Dolbier HW Solutions 423 - using disconnections in a...

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Grignard reagents are not compatible with carboxylic acids; proton transfer converts the Grignard reagent to the corresponding hydrocarbon. 19.20 ( a ) Conversion of butanoic acid to 1-butanol is a reduction and requires lithium aluminum hy- dride as the reducing agent. ( b ) Carboxylic acids cannot be reduced directly to aldehydes. The following two-step procedure may be used: ( c ) Remember that alkyl halides are usually prepared from alcohols. 1-Butanol is therefore needed in order to prepare 1-chlorobutane. ( d ) Carboxylic acids are converted to their corresponding acyl chlorides with thionyl chloride. ( e ) Aromatic ketones are frequently prepared by Friedel Crafts acylation of the appropriate acyl chloride and benzene. Butanoyl chloride, prepared in part ( d ), can be used to acylate benzene in a Friedel Crafts reaction. ( f ) The preparation of 4-octanone using compounds derived from butanoic acid may be seen by
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Unformatted text preview: using disconnections in a retrosynthetic analysis. CH 3 CH 2 CH 2 CCH 2 CH 2 CH 2 CH 3 O CH 3 CH 2 CH 2 CH CH 2 CH 2 CH 2 CH 3 OH CH 3 CH 2 CH 2 CH 2 MgBr 1 CH 3 CH 2 CH 2 CH O AlCl 3 Butanoyl chloride CH 3 CH 2 CH 2 CCl O 1 Benzene Phenyl propyl ketone CCH 2 CH 2 CH 3 O SOCl 2 Butanoic acid CH 3 CH 2 CH 2 COH O Butanoyl chloride CH 3 CH 2 CH 2 CCl O SOCl 2 CH 3 CH 2 CH 2 CH 2 OH 1-Butanol [from part ( a )] CH 3 CH 2 CH 2 CH 2 Cl 1-Chlorobutane 1. LiAlH 4 2. H 2 O PCC CH 2 Cl 2 CH 3 CH 2 CH 2 CH 2 OH 1-Butanol Butanoic acid CH 3 CH 2 CH 2 COH O Butanal CH 3 CH 2 CH 2 CH O 1. LiAlH 4 2. H 2 O CH 3 CH 2 CH 2 CH 2 OH 1-Butanol Butanoic acid CH 3 CH 2 CH 2 COH O CARBOXYLIC ACIDS 517 __ __ __...
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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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