Dolbier HW Solutions 344

Dolbier HW Solutions 344 - HCl O CH 3 CH 2 CH Propanal OH...

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17.21 ( a ) Lithium aluminum hydride reduces aldehydes to primary alcohols. ( b ) Sodium borohydride reduces aldehydes to primary alcohols. ( c ) Aldehydes can be reduced to primary alcohols by catalytic hydrogenation. ( d ) Aldehydes react with Grignard reagents to form secondary alcohols. ( e ) Sodium acetylide adds to the carbonyl group of propanal to give an acetylenic alcohol. ( f ) Alkyl- or aryllithium reagents react with aldehydes in much the same way that Grignard reagents do. ( g ) Aldehydes are converted to acetals on reaction with alcohols in the presence of an acid catalyst. O CH 3 CH 2 CH Propanal 1 2CH 3 OH Methanol CH 3 CH 2 CH(OCH 3 ) 2 Propanal dimethyl acetal
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Unformatted text preview: HCl O CH 3 CH 2 CH Propanal OH CH 3 CH 2 CHC 6 H 5 1-Phenyl-1-propanol 1. C 6 H 5 Li, diethyl ether 2. H 3 O 1 CH 3 CH 2 CH O 2. H 3 O 1 CNa, 1. HC liquid ammonia CH 3 CH 2 CHC CH OH Propanal 1-Pentyn-3-ol O CH 3 CH 2 CH Propanal OH CH 3 CH 2 CHCH 3 2-Butanol 1. CH 3 MgI, diethyl ether 2. H 3 O 1 O CH 3 CH 2 CH Propanal CH 3 CH 2 CH 2 OH 1-Propanol H 2 Ni O CH 3 CH 2 CH Propanal CH 3 CH 2 CH 2 OH 1-Propanol NaBH 4 CH 3 OH O CH 3 CH 2 CH Propanal CH 3 CH 2 CH 2 OH 1-Propanol 1. LiAlH 4 2. H 2 O 438 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP...
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