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Dolbier HW Solutions 341 - OH 3-Pentanol(achiral NaBH 4 CH...

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17.19 ( a ) First consider all the isomeric aldehydes of molecular formula C 5 H 10 O. There are three isomeric ketones: ( b ) Reduction of an aldehyde to a primary alcohol does not introduce a stereogenic center into the molecule. The only aldehydes that yield chiral alcohols on reduction are therefore those that already contain a stereogenic center. Among the ketones, 2-pentanone and 3-methyl-butanone are reduced to chiral alcohols. NaBH 4 CH 3 OH O 3-Methyl-2-butanone OH 3-Methyl-2-butanol (chiral but racemic) NaBH 4 CH 3 OH O 3-Pentanone
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Unformatted text preview: OH 3-Pentanol (achiral) NaBH 4 CH 3 OH O 2-Pentanone OH 2-Pentanol (chiral but racemic) ( R )-2-Methylbutanal ( R )-2-Methyl-1-butanol NaBH 4 CH 3 OH H O H OH H H ( S )-2-Methylbutanal ( S )-2-Methyl-1-butanol NaBH 4 CH 3 OH O OH H H 3-Pentanone 2-Pentanone 3-Methyl-2-butanone O H H ( S )-2-Methylbutanal ( R )-2-Methylbutanal 2,2-Dimethylpropanal H O H H O H Pentanal O H 3-Methylbutanal ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 435...
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