Question

Which is the major product of the reaction of cyclopentylamine and benzaldehyde followed by nickel and hydrogen? And how do you describe the mechanism?

Answer 1

Answer on Question #83023, Chemistry/Organic Chemistry

Which is the major product of the reaction of cyclopentylamine and benzaldehyde followed by nickel and hydrogen? And how do you describe the mechanism?

Answer

Reaction

Benzaldehyde cyclopentylamine benzylcyclopentylamine

Step 1 Protonation of the carbonyl oxygen

Step 2 Nucleophilic attack on the carbonyl carbon by cyclopentylamine

Step 3 Proton transfer from the nitrogen to the oxygen atom

Step 4 Elimination of water, generation of the resonance stabilized cation

Step 5 Loss of proton, formation of imine

Step 6 Reductive amination

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