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Question

The compound C4H8Cl2(A) on hydrolysis gives a compound C4H8O1(B). The compound (B) reacts with hydroxylamine and gives a negative test with Tollen's reagent. What is (A) and (B) Support your answer with proper reasoning and give the equations of reactions.

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Solution

Given that the compound (B) does not reduce Fehling solution and gives positive test for iodoform. So it is a ketone. It forms an oxime with hydroxylamine. (B) should be a methyl ketone as it forms a iodoform. As (B) is formed from (A) by hydrolysis it may be a gem dihalide. This is given in above reaction.
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