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A compound 'A' having the molecular form...

A compound 'A' having the molecular formula `C_5H_12O` on oxidation gives a compound B with molecular formula `C_5H_10O`. 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

a) `CH_3-CH_2-CH_2-CH_2-CH_2-OH`

B

b) `CH_3-CH_2-underset(OH) underset|CH_2CH-CH_3`

C

c) `CH_3-CH_2-underset(OH) underset|CH-CH_2-CH_3`

D

d) `CH_3-CH_2-underset(CH_3) underset|CH-CH_2-OH`

Text Solution

Verified by Experts

The correct Answer is:
C

Since, the compound B gave a 2,4 dinitrophenylhydrazine derivative but did not answer halogen test or silver mirror test. It must contains `a gt C=0` group, but it is neither a methyl ketone nor an aldehyde.
Moreover compound B is obtained by the oxidation of compound A, having molecular formula `C_5H_12 O`, so the compound A must be a secondary alcohol.
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