# When will organometallics act as base or nucleophile?

I would like to ask if the hydrogen next to carbonyl group is acidic,and organometallics are strong base, when will it act as a base and extracts the acidic proton and when will it attack the carbonyl carbon?

Also I would also like to ask, for bases when will it attack the acidic proton to form a enolate and when will it attack the carbonyl carbon directly to form an hemiacetal/hemiketals?

• @Dissenter since formation of water has a equilibrium constant $10^{14}$ :D – RE60K Apr 27 '15 at 15:59