An ambident nucleophile is defined here as an ion with two different kinds of nucleophilic atoms (different elements, or carbon and oxygen). Select the ambident nucleophile(s).

Athe enolate of acetone, $CH X_{2} = C (CH X_{3}) - O X^{-}$
Bthe acetate ion, $CH X_{3} COO X^{-}$
Cthe thiocyanate ion, $SCN X^{-}$
Dthe sulfite ion, $SO X_{3} X^{2 -}$

Answer: A, C, D

The enolate reacts at carbon (alkylation) or oxygen (silylation, acylation). Thiocyanate attacks through S or N, and sulfite through S or O. Acetate has two equivalent oxygens, so it is not ambident under the stated definition.

Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Electrophiles, nucleophiles, nucleophilicity and leaving groups

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An ambident nucleophile is defined here as an ion with two different kinds of nucleophilic atoms (different elements, or carbon and oxygen). Select the ambident nucleophile(s).

Answer: A, C, D

More questions on Electrophiles, nucleophiles, nucleophilicity and leaving groups