Chapter 18, Problem 18.5P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism of the given reaction is to be drawn, and the product is to be predicted.

Concept introduction:

Uncharged nucleophiles like amines can attack $\text{α,β-unsaturated}$ carbonyls at two locations – at the carbonyl carbon or at the $\text{β}$-carbon. The first one gives a $\text{1, 2-}$ or direct addition product while the second gives $\text{1, 4-}$ or conjugate addition product. Uncharged nucleophiles heavily favor conjugate addition over direct addition because it adds reversibly. The addition takes place under thermodynamic condition. Conjugate addition involves a resonance-stabilized enolate anion.