Dolbier HW Solutions 385

Dolbier HW Solutions 385 - HC O C 6 H 5 CH 2 CH 2 CHCHCH 2...

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( e ) A small amount of enol is in equilibrium with cyclopentanone. Cyclopentadienone does not form a stable enol. Enolization would lead to a highly strained allene-type compound. ( f ) The b -diketone is more extensively enolized. The double bond of the enol form of 1,4-cyclohexanedione is not conjugated with the car- bonyl group. Its enol content is expected to be similar to that of cyclohexanone. 18.22 ( a ) Chlorination of 3-phenylpropanal under conditions of acid catalysis occurs via the enol form and yields the a -chloro derivative. ( b ) Aldehydes undergo aldol addition on treatment with base.
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Unformatted text preview: HC O C 6 H 5 CH 2 CH 2 CHCHCH 2 C 6 H 5 OH 2-Benzyl-3-hydroxy-5-phenylpentanal O 2C 6 H 5 CH 2 CH 2 CH 3-Phenylpropanal NaOH ethanol, 10 8 C Cl 2 1 3-Phenylpropanal C 6 H 5 CH 2 CH 2 CH O HCl 1 2-Chloro-3-phenylpropanal C 6 H 5 CH 2 CHCH O Cl acetic acid Enol form (not particularly stable; double bond and carbonyl group not conjugated) OH O 1,4-Cyclohexanedione O O O O 1,3-Cyclohexanedione OH O Enol form (double bond conjugated with carbonyl group) H O OH (Not stable; highly strained) O Cyclopentanone OH Enol form ENOLS AND ENOLATES 479...
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