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An organic compound (A) (C5 H8 O3) on he...

An organic compound `(A) (C_5 H_8 O_3)` on heating with soda lime gives `(B)` which reacts with `HCN` to give `( C)`. The compound `( C)` reacts with thionyl chloride to produce `(D)` which on reaction with `KCN` gives a compound `( E)`. Alkaline hydrolysis of `( E)` gives a salt `(F)` which on heating with soda lime produces `n-butane`. Careful oxidation of `(A)` with dichromate give acetic acid and malonic acid. Give the structures to `(A)` to `(F)` with proper reasoning.

A

`CH_(3)-CH_(2)-overset(O)overset(||)C-CH_(2)COOH`

B

`CH_(3)CH_(2)underset(OH)underset(|)CHCH_(2)COOH`

C

`CH_(3)overset(O)overset(||)C"C"H_(2)CH_(2)COOH`

D

`CH_(3)CH_(2)underset(OH)underset(|)CHCOOH`

Text Solution

Verified by Experts

The correct Answer is:
A
(a) As the compound [A] upon oxidation gives `CH_(3)COOH" and "H_(2)C(COOH)_(2),` the structure (a) is the correct structure.
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