Dolbier HW Solutions 379

Dolbier HW Solutions 379 - 473 ENOLS AND ENOLATES 18.10 (b)...

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18.10 ( b ) Approaching this problem mechanistically in the same way as part ( a ), write the structure of the enolate ion from 2-methylbutanal. This enolate adds to the carbonyl group of the aldehyde. A proton transfer from solvent yields the product of aldol addition. ( c ) The aldol addition product of 3-methylbutanal can be identi f ed through the same mechanis- tic approach. O (CH 3 ) 2 CHCH 2 CH CHCH(CH 3 ) 2 2 HC O 3-Hydroxy-2-isopropyl-5-methylhexanal OH (CH 3 ) 2 CHCH 2 CH CHCH(CH 3 ) 2 1 OH 2 HC O 3-Methylbutanal Enolate of 3-methylbutanal 1 O (CH 3 ) 2 CHCH 2 CH CHCH(CH 3 ) 2 2 HC O H 2 O 1 H 2 O 1 HO 2 O (CH 3 ) 2 CHCH 2 CH 3-Methylbutanal
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