Question

Which of the following are ambident nucleophiles?

• A. ${\mathrm{Br}}^{–}$
• B. ${\mathrm{CN}}^{–}$
• C. ${{\mathrm{NO}}_2}^{–}$
• D. Both (B) and (C)

Answer 1

The correct option is D

Both (B) and (C)

Explanation for the correct option:

Option (D) Both (B) and (C)

• Ambident nucleophiles are nucleophiles with two nucleophilic sites.
• Because both atoms of ${{\mathrm{NO}}_2}^{-}$ and ${\mathrm{CN}}^{-}$ can donate an electron, they are both ambident nucleophiles.
• ${{\mathrm{NO}}_2}^{-}$ can donate electrons via nitrogen and oxygen atom while ${\mathrm{CN}}^{-}$ can donate electrons via nitrogen and carbon atom

Explanation for the incorrect options:

(A) ${\mathrm{Br}}^{–}$

There aren't two nucleophilic sites on it. Thus, this is the wrong choice.

Therefore, Option (D), Both (C) and (D) is correct.