Dolbier HW Solutions 377

Dolbier HW Solutions 377 - 471 ENOLS AND ENOLATES 18.2 As...

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ENOLS AND ENOLATES 471 18.2 As shown in the general equation and the examples, halogen substitution is specifc For the a -carbon atom. The ketone 2-butanone has two nonequivalent a carbons, and so substitution is possible at both positions. Both 1-chloro-2-butanone and 3-chloro-2-butanone are Formed in the reaction. 18.3 The carbon–carbon double bond oF the enol always involves the original carbonyl carbon and the a -carbon atom. 2-Butanone can Form two diFFerent enols, each oF which yields a diFFerent a -chloro ketone. 18.4 Chlorine attacks the carbon–carbon double bond oF each enol. 18.5 ( b ) Acetophenone can enolize only in the direction oF the methyl group. ( c ) Enolization oF 2-methylcyclohexanone can take place in two diFFerent directions.
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