Count the ambident nucleophiles in the following list. Counting convention: a species is ambident if it has two different kinds of atoms (different elements) that can each attack an electrophile; two equivalent atoms (such as the two oxygens of a carboxylate) do not count. Species: $CN X^{-}$ , $NO X_{2} X^{-}$ , $SCN X^{-}$ , $OCN X^{-}$ , $SO X_{3} X^{2 -}$ , $CH X_{3} COO X^{-}$ , $N X_{3} X^{-}$ , $Cl X^{-}$ , $OH X^{-}$ , $CH X_{3} O X^{-}$ , $(CH X_{3}) X_{3} C - O X^{-}$ . Give the number as an integer.

Numerical answer type, tolerance 0.5.

Answer: 5

Cyanide (C or N), nitrite (N or O), thiocyanate (S or N), cyanate (O or N) and sulfite (S or O) each have two different attacking elements. Acetate has two equivalent oxygens, azide's terminal nitrogens are equivalent, and

Cl X^{-}

OH X^{-}

CH X_{3} O X^{-}

and tert-butoxide have one kind of nucleophilic atom. The count is 5.

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

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Answer: 5

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