{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

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

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

View Full Document Right Arrow Icon
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 )
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

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 __ __ __...
View Full Document

{[ snackBarMessage ]}