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  4. Imine formation using an aldehyde/ketone and primary amine is acid-catalyzed, yet the rate drops below pH 4.5. Why does the rate drop below this pH?

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Q. Imine formation using an aldehyde/ketone and primary amine is acid-catalyzed, yet the rate drops below pH 4.5. Why does the rate drop below this pH?

NTA AbhyasNTA Abhyas 2020Aldehydes Ketones and Carboxylic Acids

Solution:

Imine formation:

Solution

The reaction is possible pH 4 to 5 only. Hence, the reaction is pH dependent.

At very low pH (high conc. of $H^{+}$ ): ammonia derivative will form their respective salts due to their basic nature and at the same time will lose their nucleophilic nature.

At very high pH (high conc. of $OH^{-}$ ): carbonyl group will not be able to undergo sufficient protonation.