An organic compound (A) `(C_(5)H_(7)OCl)` reacts rapidly with ethanol to give (B) `(C_(7)H_(12)O_(2))`. (A) also reacts with water to produce an acid which reacts with bromine to give (C ) `(C_(5)H_(8)Br_(2)O_(2))`. (B) on boiling with `H_(2)SO_(4)` forms an acid (D). When (D) is oxidised with `KMnO_(4)` an acid (E ) `(C_(4)H_(6)O_(3))` is produced. On mild heating, (E ) gives (F) `(C_(3)H_(6)O)` which cannot be oxidised by ammoniacal `AgNO_(3)`. Identify the compounds (A) to (F).

Explanation

(A) `implies C_(5)H_(7)OCI`, Degree of unsaturation: `2^(@)`
(B) `implies` Degree of unsaturation: `2^(@)`

`implies` (F) (not, aldehyde may be a ketone)

`C_(5)H_(8)Br_(2)O_(2)` [This shows `C=C` ]
`(F) rArr` Ketone (three C atoms), only ketone with three C atoms is acetone `(CH_(3)-CO-CH_(3))`.
So, (E ) can be `[CH_(3)-overset(O)overset(||)C-CH_(2)-COOH]`
because keto acid on heating loses `CO_(2)` and gives ketone.
(D) `overset([O])rarr` Acid (E ) `C_(4)H_(6)O_(3)` [So, (D) contains `(C=C)`]
Hence, (D) can be `(CH_(2)=underset(CH_(3))underset(|)C-CH_(2)-COOH)`
`(A) implies R-overset(O)overset(||)C-Cl overset(HOC_(2)H_(5))rarr R-overset(O)overset(||)C underset((Ester))underset((B))-OC_(2)H_(5)`
`(A) implies CH_(2)=underset(CH_(3))underset(|)C-CH_(2)-overset(O)overset(||)C-Cl`
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