Dolbier HW Solutions 380

Dolbier HW Solutions 380 - 1 HO 2 O (CH 3 ) 3 CCCH 3...

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18.11 Dehydration of the aldol addition product involves loss of a proton from the a -carbon atom and hydroxide from the b -carbon atom. ( b ) The product of aldol addition of 2-methylbutanal has no a hydrogens. It cannot dehydrate to an aldol condensation product. ( c ) Aldol condensation is possible with 3-methylbutanal. 18.12 The carbon skeleton of 2-ethyl-1-hexanol is the same as that of the aldol condensation product derived from butanal. Hydrogenation of this compound under conditions in which both the carbon carbon double bond and the carbonyl group are reduced gives 2-ethyl-1-hexanol. 18.13 ( b ) The only enolate that can be formed from tert -butyl methyl ketone arises by proton abstrac- tion from the methyl group.
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Unformatted text preview: 1 HO 2 O (CH 3 ) 3 CCCH 3 tert-Butyl methyl ketone Enolate of tert-butyl methyl ketone O (CH 3 ) 3 CCCH 2 2 CH 3 CH 2 CH 2 CH O Butanal 2-Ethyl-1-hexanol CH 3 CH 2 CH 2 CH 2 CHCH 2 OH CH 2 CH 3 CH 3 CH 2 CH 2 CH O CCH CH 2 CH 3 2-Ethyl-2-hexenal H 2 , Ni NaOH, H 2 O heat HO 2 2(CH 3 ) 2 CHCH 2 CH O 3-Methylbutanal (CH 3 ) 2 CHCH 2 CHCHCH(CH 3 ) 2 HO HC O Aldol addition product (CH 3 ) 2 CHCH 2 CH CCH(CH 3 ) 2 HC O 2-Isopropyl-5-methyl-2-hexenal 2 H 2 O 2CH 3 CH 2 CHCH CH 3 O HO 2 2-Methylbutanal CH 3 CH 2 CHCH CH 3 HO CCH 2 CH 3 HC O CH 3 a (No protons on a-carbon atom) 1 H 2 O 1 HO 2 R 2 C CHCH O CHCH H O OH 2 R 2 C OH heat 474 ENOLS AND ENOLATES...
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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