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An organic compound 'A' (C(4)H(10)O) is ...

An organic compound `'A' (C_(4)H_(10)O)` is optically active. On mild oxidation, it gives a compound `'B' (C_(4)H_(8)O)` but upon vigorous oxidation, it gives another compound `'C' (C_(3)H_(6)O_(2))`. The compound `'C'` along with `'D'` are also formed from `'B'` by reacting with iodine in the presence of alkali. Deduce the structures of `'A', 'B', 'C'` and `'D'`.

Text Solution

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The data suggests that the compound 'A' `(C_(4)H_(10)O)` is an alcohol. Since it is optically active in nature, it is a secondary alcohol. The alcohol upon mild oxidation gives ketone `'B' (C_(4)H_(8)O)`. The compound `'A'` on vigouus oxidation forms an acid `'C' (C_(3)H_(6)O_(2))`. The acid `'C'` and a compoun D (iodoform) are formed are when 'B' is reacted with iodine and alkali `(NaOH)`. The sequenc of reactions is given ahead:
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