DAT destroyer 2009 Orgo question #14

[Innulja]

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reaction of cyclohexanone with excess Cl2 in acid.
As far as I know in acid it removes only one alpha hydrogen, and monochlorinated product results, where as under basic conditions, each successive bromination increases the acidity of the renaming alpha hydrogen atoms.
Is this the mistake in destroyer or can anyone explain what is the reasoning behind the answer.
Thank you

 

[wantVCUdental]

The answer is correct, and this question has been discussed before.

Just remember, chlorination is a wacky process and highly reactive, usually chlorination gives a mixture of products

If you think about it, it also makes sense, chlorine is electron withdrawing thereby making the protons more acidic, because the negative lone pair that's left after a proton leaves can inductively stabilize with help of chlorine.

Hope this helps