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for water (weak nucleophile) to attack, the carbonyl group must first be activated by protonation, deprotonation then gives the hydrate
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- nitrogen nucleophile strong (N less electronegative), attacks the carbonyl carbon without activation
- RONa (alkoxide), NaCN (cyanide), NaSH (sulfanide), RMgBr (grignard carbocation), LAH (hydride), could be H3O+, need water in a following step
- the unhydrated keto form (carbonyl) more than for aldehydes (aldehydes are more reactive)