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carbonnyl group + H2N--Z gives the carbon double bonded to the N-Z and water
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- amine attacks carbonyl group, oxygen protonated to remove negative charge, deprotonation gives a carbinolamine (H taken from the N), OH group protonated into a good leaving group, water leaves, C=N double bond forms, intermediate deprotonated to generate enamine
- gives cyclohexenones and is a Michael addition followed by internal Aldol condensation
- hydroxide in an SN2 process opens the ring, resulting alkoxide ion protonated by water