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Which double bond is more electrophilic : carbon-carbon double bond or carbon- oxygen double bondoxygen?

Question enter image description here

cyclopent-2-en-1-one and gilman's reagent with acid workup

Attempt

It seems to me that the carbon oxygen-oxygen bond would be more electrophilic due to the higher electronegativity of Oxygenoxygen. Hence I believe CH3$\ce{CH3-}$ 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 CH3-$\ce{CH3-}$ attacked carbon- carbon double bond?

What can be thea valid reason?

Which bond is more electrophilic : carbon-carbon double bond or carbon- oxygen double bond?

Question enter image description here

Attempt

It seems to me that the carbon oxygen bond would be more electrophilic due to higher electronegativity of Oxygen. Hence I believe 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 CH3- attacked carbon- carbon double bond?

What can be the valid reason?

Which double bond is more electrophilic : carbon-carbon or carbon-oxygen?

Question

cyclopent-2-en-1-one and gilman's reagent with acid workup

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?

Source Link

Which bond is more electrophilic : carbon-carbon double bond or carbon- oxygen double bond?

Question enter image description here

Attempt

It seems to me that the carbon oxygen bond would be more electrophilic due to higher electronegativity of Oxygen. Hence I believe 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 CH3- attacked carbon- carbon double bond?

What can be the valid reason?