The reaction of ethyl methyl ketone with Cl_2 | vedclass

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Question

(B) The reaction of ethyl methyl ketone $(CH_3CH_2COCH_3)$ with $Cl_2$ in the presence of excess $OH^{-}$ is a haloform-type reaction (specifically,ch

Vedclass · Accepted Answer

$CH_3CH_2COCCl_3$

Vedclass · Answer

(B) The reaction of ethyl methyl ketone $(CH_3CH_2COCH_3)$ with $Cl_2$ in the presence of excess $OH^{-}$ is a haloform-type reaction (specifically,chlorination of the $\alpha$-carbon). Since the methyl group $(CH_3)$ attached to the carbonyl is more sterically accessible and the resulting enolate is more stable for further substitution,the chlorination occurs preferentially at the methyl group. The $\alpha$-hydrogens of the methyl group are successively replaced by chlorine atoms due to the inductive effect of the chlorine atoms,which makes the remaining $\alpha$-hydrogens even more acidic. Ultimately,the methyl group is converted into a trichloromethyl group $(-CCl_3)$,resulting in the product $CH_3CH_2COCCl_3$.

The reaction of ethyl methyl ketone with $Cl_2$ / excess $OH^{-}$ gives the following major product:

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