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Amine conjugate addition 3

The product of an amine conjugate addition is still an amine, which can attack another molecule if it has a proton to lose:


This can even happen in the same molecule:


Notice that the hydroxylamine always attacks using the lone pair on nitrogen, not oxygen. Nitrogen is a better nucleophile. This is obvious from experimental data, but can also be viewed from a MO perspective - nitrogen is more electropositive so its lone pair is higher in energy.

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