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Among the following species, which one has the highest nucleophilicity?

1. CH3(-)
2. NH2(-)
3. CH3O(-)
4. (CH3)3CO(-)

Correct answer: CH3(-)

Solution

Nucleophilicity increases as the electronegativity of the atom bearing the lone pair decreases. Carbon is the least electronegative among C, N, O, so CH3(-) (carbanion) holds its electron pair most loosely and attacks electrophiles most readily.

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