1. The problem statement, all variables and given/known data I have a general question about keto-enol mechanisms. In a carbonyl compound, the carbonyl carbon is susceptible to nucleophilic attack. This is clearly different from what happens in base/acid catalyzed keto-enol tautomers. How can nucleophilic attack be avoided in a base solution in order to promote the keto-enol form? 2. Relevant equations N/A 3. The attempt at a solution When I looked at the examples from my book on keto-enol (a base such as OH- involved), I couldn't help but wonder why that OH- in solution didn't act as a nucleophile instead of abstracting the alpha hydrogen. Why is this and what am I missing here? Does this perhaps have something to do with the acidity of the alpha hydrogens?