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(Solved): 5. Give the mechanism of the following reaction: PhC(CH2CH3)NNH2(KOH,175C,HOCH2 ...

$5. Give the mechanism of the following reaction: \( \mathrm{PhC}\left(\mathrm{CH}_{2} \mathrm{CH}_{3}\right) \mathrm{NNH}_{2}$

5. Give the mechanism of the following reaction:

PhC (CH_{2} CH_{3}) NNH_{2} ? (KOH, 17 5^{?} C, HOCH_{2} CH_{2} OCH_{2} CH_{2} OH)

? PhCH_{2} CH_{2} CH_{3} + N_{2} (4)

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The given reaction is the Hoffmann degradation of a primary amide, specifically PhC(CH2CH3)NNH2. The reaction is carried out under specific conditions involving KOH (potassium hydroxide) and a solvent such as diethylene glycol (HOCH2CH2OCH2CH2OH).

Mechanism: Step 1: Formation of the carbonyl anion The reaction begins with the deprotonation of the amide nitrogen by the strong base KOH. The lone pair of electrons on the nitrogen attacks the hydrogen atom of the hydroxide ion, resulting in the formation of the carbonyl anion.

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