An organic compound X is oxidized by using acidified K 2 C r 2 O 7 . The product obtained reacts with phenyl…

An organic compound X is oxidized by using acidified K 2 C r 2 O 7 . The product obtained reacts with phenyl hydrazine, but does not answer silver mtextrror test. The possible structure of X is
  1. C H 3 C O C H 3
  2. C H 3 2 C H O H
  3. C H 3 C H O
  4. C H 3 C H 2 O H

Solution

The oxidation product of X reacts with phenyl hydrazine, thus it contains > C = 0 group. The same product does not give silver mirror test. Thus, it is a ketone, because only aldehydes give silver mirror test.
Thus, the compound X must be 2 o alcohol, as only secondary alcohols give ketones on oxidation and hence, X is C H 3 2 C H O H . .

Asked in: JEE-TOPICTESTS-CHEMISTRY

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