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The product formed with water is stable only due to resonance, but does not form a very stable equilibrium.
Enamine reactions are used to avoid many problems usually associated with alkylating or acylating carbonyl compounds when they are reacted with aqueous sodium hydroxide1 as shown in reactions (ii) and (iv)1. The main problem being that the reaction results in a great number of crucial secondary side reactions, such as those in equations (iii), (iv) and (vi), and this in turn results in the main product formed in (i) being only available in small amounts because of the previously mentioned unstable equilibrium, while nucleophile OH- in equation (iii) is much higher1...
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