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If the alpha - hydrogen of a Carbon - Carbon double bond increases, then its stability increases. So, its nucleophilicity should decrease. But at the same time, a +H and +I group like CH3 should also increase the magnitude of negative charge on C=C.

So does nucleophilicity increase for an alkene with increase in alpha hydrogen?

Apologies if this is a dupes, but I could not find an answer on Google search.

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  • $\begingroup$ Hmm, I think sterics would be a bigger issue. $\endgroup$
    – Mithoron
    Commented Jul 28 at 12:40

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When the number of alpha carbons increases, the +I effect causes the electron density on the carbon of the C=C bonds to increase, making this double bond act like a nucleophile. Note that if the number of alpha hydrogens increases, for example, with more -CH3 groups, it causes steric hindrance and reduces their nucleophilicity.

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