Dolbier HW Solutions 387

Dolbier HW Solutions 387 - that can undergo dehydration O O...

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( d ) The reaction is a mixed aldol condensation. The enolate of 2,2-diphenylcyclohexanone reacts with p -chlorobenzaldehyde. Elimination of the aldol addition product occurs readily to yield the a , b -unsaturated ketone as the isolated product. ( e ) The aldehyde given as the starting material is called furfural and is based on a furan unit as an aromatic ring. Furfural cannot form an enolate. It reacts with the enolate of acetone in a manner much as benzaldehyde would. ( f ) Lithium dialkylcuprates transfer an alkyl group to the b -carbon atom of a , b -unsaturated ketones. A mixture of stereoisomers was obtained in 67% yield in this reaction. ( g ) Two nonequivalent a -carbon atoms occur in the starting ketone. Although enolate formation is possible at either position, only reaction at the methylene carbon leads to an intermediate
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Unformatted text preview: that can undergo dehydration. O O CHC 6 H 5 OH HO 2 C 6 H 5 CHO 2 H 2 O O CHC 6 H 5 Observed product (75% yield) LiCu(CH 3 ) 2 1 CH 3 CH 3 O H 3 C 1. diethyl ether 2. H 2 O 2,4,4-Trimethyl-2-cyclohexenone CH 3 CH 3 CH 3 O H 3 C 2,3,4,4-Tetramethyl-cyclohexanone 1 O NaOH water 2 H 2 O CH O O Furfural CH 3 CCH 3 Acetone CHCH 2 CCH 3 OH O O (Not isolated) CH CHCCH 3 O O 4-Furyl-3-buten-2-one (60 – 66%) 1 CH Cl C 6 H 5 C 6 H 5 O KOH ethanol 2 H 2 O CH O Cl p-Chlorobenzaldehyde C 6 H 5 C 6 H 5 O 2,2-Diphenylcyclo-hexanone CH OH Cl C 6 H 5 C 6 H 5 O (Not isolated) 2-( p-Chlorobenzylidene)-6,6-diphenylcyclohexanone (84%) ENOLS AND ENOLATES 481...
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