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Question: A compound ‘A’ having the molecular formula \(\mathrm { C } _ { 5 } \mathrm { H } _ { 10 } \mathrm {...

A compound ‘A’ having the molecular formula C5H10O\mathrm { C } _ { 5 } \mathrm { H } _ { 10 } \mathrm { O }. Compound ‘B’ gave a 2,4 dinitrophenylhydrazine derivative but did not answer haloform test or silver mirror test. The structure of compound ‘A’ is

A

CH3CH2CH2CH2CH2OH\mathrm { CH } _ { 3 } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { CH } _ { 2 } - \mathrm { CH } _ { 2 } - - \mathrm { OH }

B

C

D

Answer

Explanation

Solution

:

Since (2) on reaction with 2,4- DNP forms a derivative it implies that (2) has fig.

(2) gives –Ve Tollens’ test, hence it is not an aldehyde, but it is a ketone.

(2) gives –ve haloform test, thus it is not a methyl ketone.

(2) is formed from the oxidation of (1), thus (1) is a 20 alcohol and among the given options.,

(1) is :

And is