**Question** [![cyclopent-2-en-1-one and gilman's reagent with acid workup][1]][1] **Attempt** It seems to me that the carbon-oxygen bond would be more electrophilic due to the higher electronegativity of oxygen. Hence I believe $\ce{CH3-}$ should attack the carbonyl site. But this doesn't seem to be the case. Is it because that the intermediate carbanion can undergo resonance with oxygen, had $\ce{CH3-}$ attacked carbon- carbon double bond? What can be a valid reason? [1]: https://i.sstatic.net/NkI1L.png