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?


Grignard is a base as well as an nucleophile. When there's a strong electron deficient group it'll attack there, when there' a very acidic group it'll attack there. For other bases it depends upon their relative basicity and nucleophilicity. BAsicity is thermodynamically related while nucleophiicity is kinetically decide. They're silent about each other. You need to practice and gather examples and an experience too :D

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  • $\begingroup$ I like this answer! Especially the delineation between thermodynamics and kinetics, $\endgroup$ – Dissenter Apr 26 '15 at 18:01
  • $\begingroup$ @Dissenter happy to hear a word from from you since a long time :D $\endgroup$ – RE60K Apr 27 '15 at 5:10
  • $\begingroup$ I will add that acid-base reactions tend to be kinetically favored over other reactions. $\endgroup$ – Dissenter Apr 27 '15 at 15:38
  • $\begingroup$ @Dissenter since formation of water has a equilibrium constant $10^{14}$ :D $\endgroup$ – RE60K Apr 27 '15 at 15:59

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