NTA Abhyas JEE Main2020ChemistryAldehydes and KetonesPractice
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?
Options
- AThe carbinolamine intermediate is stable at low pH
- BThe imine product is hydrolyzed at low pH
- CProtonation of the amine decreases its nucleophilicity
- DThe amine is hydrolyzed at low pH
Correct answer
C. Protonation of the amine decreases its nucleophilicity
Step-by-step solution
Imine formation: 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 O H - ): carbonyl group will not be able to undergo sufficient protonation.