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Explain Wolf-Kishner reduction reaction. - Chemistry

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प्रश्न

Explain Wolf-Kishner reduction reaction.

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उत्तर

The carbonyl group of aldehydes and ketones is reduced to the methylene group \[\ce{[- CH2 -]}\] on treatment with hydrazine followed by heating with sodium or potassium hydroxide in a high-boiling solvent like ethylene glycol, known as the Wolf-Kishner reduction.

\[\begin{array}{cc}
\ce{O}\phantom{...................................}\\
||\phantom{.....................}\backslash\phantom{.............}\\
\ce{C + \underset{(Hydrazine)}{NH2 - NH2} ->[-H2O] \underset{(Hydrazone)}{C = N - NH2}}\\
/\phantom{..}\backslash\phantom{....................}/\phantom{..............}\\
\end{array}\]

 

\[\begin{array}{cc}
\backslash\phantom{.............................}\backslash\phantom{..............}\\
\ce{\underset{(Hydrazone)}{C = N - NH2} ->[KOH, \Delta][Ethylene glycol] \underset{(Methyl group)}{CH2} + N2}\\
/\phantom{.............................}/\phantom{..............}\\
\end{array}\]

Here the oxygen of the carbonyl group is replaced by two hydrogen atoms.

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Chemical Properties of Aldehydes and Ketones
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Answer in brief.

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\[\begin{array}{cc} \phantom{...}\ce{R}\phantom{....}\ce{OR'}\phantom{}\\ \phantom{}\backslash\phantom{..}/\\ \ce{C}\\ \phantom{}/\phantom{..}\backslash\\ \phantom{...}\ce{H}\phantom{....}\ce{OR'}\phantom{} \end{array}\]


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\[\begin{array}{cc}
\ce{CH3 - CH2 - CH2 - C - CH3 ->[HO - CH2 - CH2 - CH2 - OH][dry HCl] ?}\\
||\phantom{.........}\\
\ce{O}\phantom{.........}
\end{array}\]


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\[\begin{array}{cc}
\ce{O}\phantom{........}\\
||\phantom{........}\\
\ce{\underset{(Acetone)}{CH3 - C - CH3}->[CrO3] B}
\end{array}\]


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