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[yalla22]

what happens when you add a strong nucleophile (R2-N-H) under ACIDIC conditions to an aldehyde?

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[liverotcod]

Under acidic conditions, an amine is not a strong nucleophile, since it will be protonated and have no lone pair to go shopping for positive charge.

 

[liverotcod]

On the other hand, under less acidic conditions (pH 4.7), primary amines can react with carbonyls to form imines: H2N-Z + CHO -> RC=N-Z + H2O, which can then be reduced to the secondary amine.