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Base Catalysed Hydrolysis of Esters

An aromatic c...

Question

An aromatic compound $(X)$ $(C_{8} H_{8} O)$ gives positive 2,4-DNP test. It gives a yellow precipitate of compound $(Y)$ on reaction with iodine and sodium hydroxide solution. $(X)$ does not give Tollen's test on oxidation under drastic conditions. It gives a carboxylic acid $(Z)$ $(C_{7} H_{6} O_{2})$ . $(Z)$ is also formed with $(Y)$ during the reaction. $(X), (Y)$ and $(Z)$ respectively are:

A

C_{6} H_{5} C O C H_{3}, C H I_{3}, C_{6} H_{5} C O O H

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B

C H_{3} C O C H_{3}, C H I_{3}, C H_{3} C O O H

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C

C_{6} H_{5} C O C H_{3}, C H I_{3}, C H_{3} C O O H

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D

C H_{3} C H O, C H I_{3}, C_{6} H_{5} C O O H

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Solution

The correct option is A $C_{6} H_{5} C O C H_{3}, C H I_{3}, C_{6} H_{5} C O O H$
$X = C_{8} H_{8} O$ should ketone because it gives $2, 4 -$ DNP not tollen's reagent
Therefore (Image 1)
Z formed with $4$ also while Iodoform test .
Hence from above reaction.
(Image 2)

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C_{8} H_{8} O

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C_{8} H_{8} O

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