An organic compound X is oxidized by using acidified K2 C r2 O7 . The product obtained reacts with phenyl hydrazine, but does not answer silver mirror test. The possible structure of X is

Question

An organic compound X is oxidized by using acidified K2 C r2 O7 . The product obtained reacts with phenyl hydrazine, but does not answer silver mirror test. The possible structure of X is (A) CH 3 COCH 3 (B) ( CH 3)2 CHOH (C) CH 3 CHO (D) CH 3 CH 2 OH

Tardigrade Admin · Accepted Answer

Secondary alcohols on oxidation with K 2 Cr 2 O 7 form ketone, ketones react with phenyl hydrazine to form hydrazone but does not react with Tollen's reagent. H3C - underset overset|CH3 overset underset|HC -OH ->[K2Cr2O7][H2SO4] CH3 - underset overset|CH3C = O +H2O

Q. 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 mirror test. The possible structure of $X$ is

$C H_{3} COC H_{3}$

$(C H_{3})_{2} C H O H$

$C H_{3} C H O$

$C H_{3} C H_{2} O H$

Secondary alcohols on oxidation with $K_{2} C r_{2} O_{7}$ form ketone, ketones react with phenyl hydrazine to form hydrazone but does not react with Tollen's reagent.
$H_{3} C - C H_{3} ∣ C ∣ H - O H K_{2} C r_{2} O_{7} H_{2} S O_{4} C H_{3} - C H_{3} ∣ C = O + H_{2} O$

Q. An organic compound X is oxidized by using acidified K2​Cr2​O7​. The product obtained reacts with phenyl hydrazine, but does not answer silver mirror test. The possible structure of X is

CH3​COCH3​

(CH3​)2​CHOH

CH3​CHO

CH3​CH2​OH