Dolbier HW Solutions 399 - O CH 3 O HCCH 2 CH 2 CHCCH 3 1...

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( b ) The starting material, known as citral, is converted to the two products by a reversal of an aldol condensation. The fi rst step is conjugate addition of hydroxide. The product of this conjugate addition is a -hydroxy ketone. It undergoes base-catalyzed cleavage to the observed products. ( c ) The product is formed by an intramolecular aldol condensation. ( d ) In this problem stereochemical isomerization involving a proton attached to the -carbon atom of a ketone takes place. Enolization of the ketone yields an intermediate in which the
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Unformatted text preview: O CH 3 O HCCH 2 CH 2 CHCCH 3 1 HO 2 O CH 3 O HCCH 2 CH 2 CHCCH 2 1 H 2 O 2 HC CH 3 O CH 2 O 2 C H 2 O CH 2 CH 3 O CH 3 O H HO HO 2 ( 2 H 2 O) CH 3 O H 2 O OH CHCH 2 CH 2 C (CH 3 ) 2 C CH 3 CH 2 CH O HO 2 CH 3 CH O O CHCH 2 CH 2 C (CH 3 ) 2 C CH 3 CH 2 CH O 2 O CHCH 2 CH 2 CCH 3 (CH 3 ) 2 C 1 H 2 C CH O 2 H 2 O (CH 3 ) 2 C CH 3 OH CHCH 2 CH 2 C CH CH O O 2 O (CH 3 ) 2 C CH 3 OH CHCH 2 CH 2 C CH CH (CH 3 ) 2 C CH 3 OH CHCH 2 CH 2 C CH 2 CH H 2 O 2 ENOLS AND ENOLATES 493...
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