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An organic compound [A] with molecular f...

An organic compound [A] with molecular formula `C_(5)H_(8)O_(2)` is reduced to n-pentane on treatment with `Zn-Hg//HCl`. The compound [A] forms a dioxime with hydroxyl amine and give a positive iodoform test and Tollen's test. Identify the compound [A] and deduce its structure?

Text Solution

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(i) Compound .A. must be an aldehyde or ketone containing 5 carbon atoms in a chain.
(ii) As it gives +ve Tollens test, hence it must be an aldehyde.
(iii) As it forms dioxime, hence compound must contain two aldehydic groups.
Thus compound .A. is `CHO-(CH_(2))_(3)-CHO`
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