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An organic compound (A) on treatment wit...

An organic compound `(A)` on treatment with ethyl alcohol gives a carboxylic acid `(B)` and compound `( C)`. The hydrolysis of `( C)` under acidic conditions gives `(B)` and `(D)`. Oxidation of `(D)` with `KMnO_4` also gives `(B)`. `(B)` on heating with `Ca(OH)_2` gives `(E)` (molecular formula, `C_3 H_6 O`). `(E)` does not give Tollens test and does not reduce Fehling's solution but forms a `2,4-`dinitrophenyl hydrazone. Identify `(A),(B), ( C), (D)`, and `(E)`.

Text Solution

Verified by Experts

`(A) + C_(2) H_(5) OH rarr ( B ) + ( C ) `
`( C ) overset( H_(2) O^(+))(rarr) (B) +(D) underset( KMnO_(4))overset( (O))(rarr) (B)`

`rArr` E is certainly ketone.
i.e., E is `CH_(3) - underset( O ) underset( ||)(C) - CH_(3) ( C_(3) H_(6)O)`
Calcium salt of B gives E on heating , hence B is `CH_(3)COOH`.
According D will be `CH_(3) CH_(2) OH` . Clearly ( C ) is an ester.
C is `CH_(3) -overset( O ) overset( ||)(C) - OC_(2)H_(5)overset( H_(3)O^(+))(rarr) CH_(3) -overset( O)overset( ||)(C) -OH + C_(2) H_(5) OH`
`( A) overset( C_(2)H_(5)OH)( rarr) underset((B))(CH_(3)COOH)+underset((C ))(CH_(3)-overset(O)overset(||)(C)-OC_(2)H_(5)OH)`
Hence A is anhydride.
A is `:`
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