Question

An organic compound 'A' with molecular formula C₅H₈O₂ is reduced to n-pentane with hydrazine followed by heating with NaOH and glycol. 'A' forms a dioxime with hydroxylamine and gives a positive iodoform and Tollen's test. Identify 'A' and give its reaction for iodoform and Tollen's test.

Answer 1

Molecular formula = C₅H₈O₂ (given)

Structural formula:

\[\begin{array}{cc}
\phantom{...}\ce{O}\phantom{.............}\ce{O}\phantom{}\\
\phantom{...}||\phantom{..............}||\phantom{}\\
\ce{CH3-C-CH2-CH2-C-H}
\end{array}\]

Compound 'A' Hydrazine:

\[\ce{CH3-CH2-CH2-\underset{n-pentane}{CH2-CH3} + 2H2O}\]

\[\begin{array}{cc}
\phantom{...............}\ce{O}\phantom{.............}\ce{O}\phantom{....................}\ce{NOH}\phantom{..........}\ce{NOH}\phantom{.....................}\ce{O}\phantom{..............}\ce{O}\phantom{.............}\\
\phantom{.................}||\phantom{..............}||\phantom{....................}||\phantom{..............}||\phantom{.........................}||\phantom{..............}||\phantom{................}\\
\ce{CH3-C-CH2-CH2-C-H ->[2NH2OH]\underset{dioxime}{CH3-C-CH2}-CH2-C-H ->[Tollen's Reagent] CH3-C-CH2-CH2-C-OH}\\
\end{array}\]

\[\begin{array}{cc}
\ce{O}\phantom{........................................................}\\
||\phantom{........................................................}\\
\ce{CH3-C-CH2-CH2-CHO ->[NaOH][I2] NaOOC-CH2-CH2-CHO + \underset{Iodoforrn}{CHI3}}
\end{array}\]