ENOLS AND ENOLATES 473 18.10 (b) Approaching this problem mechanistically in the same way as part(a), write the structure of the enolate ion from 2-methy lbutana CHaCH,CHCH HO- CHaCH, CCH →CH3CH2C=CH H3 2-Methylbutanal Enolate of 2-methylbutanal This enolate adds to the carbonyl group of the aldehyde CH CH3CH CHCH CCH,,CH3 CHCH2CHCH— CCH,CH CH 2-Methylbutanal Enolate of A proton transfer from solvent yields the product of aldol addition. 0 CH CH CHCHCH--CCH,CH HO CH-CH, CHCH--CCH,CH, +HO CH3 HC=O (c) The aldol addition product of 3-methylbutanal can be identified through the same mechanis (CH3)2 CHCH,CH HO (CH )2CHCHCH H,O 3-Methylbutanal Enolate of 3-methylbutanal H3) CH +CHCH(CH3)2(CH])2CHCH2 CH-CHCH(CH3) 3-Methylbutanal Enolate of 3-methylbutanal (CH), CHCH, CH--CHCH(CH)2+ OH 3-Hydroxy-2-isopropyl-5-methylhexanal Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website18.10 (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 identified through the same mechanis￾tic approach. O (CH3)2CHCH2CH CHCH(CH3)2 HC O 3-Hydroxy-2-isopropyl-5-methylhexanal OH (CH3)2CHCH2CH CHCH(CH3)2 OH HC O 3-Methylbutanal Enolate of 3-methylbutanal O (CH3)2CHCH2CH CHCH(CH3)2 HC O H2O HO H2O O (CH3)2CHCH2CH 3-Methylbutanal O (CH3)2CHCHCH Enolate of 3-methylbutanal HO HO CH3CH2CHCH CH3 CCH2CH3 CH3 HC O H2O O CH3CH2CHCH CH3 CCH2CH3 CH3 HC O 2-Ethyl-3-hydroxy-2,4- dimethylhexanal O CH3CH2CHCH CH3 2-Methylbutanal Enolate of 2-methylbutanal CCH2CH3 CH3 HC O O CH3CH2CHCH CH3 CCH2CH3 CH3 HC O HO O CH3CH2CHCH CH3 2-Methylbutanal Enolate of 2-methylbutanal O CH3CH2CCH CH3 O CH3CH2C CH CH3 ENOLS AND ENOLATES 473 Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website