Question:
Which of the following is an ambident nucleophile?
Which of the following is an ambident nucleophile?
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Other common ambident nucleophiles to remember for exams are $NO_2^-$ (Nitrito/Nitro) and $SCN^-$ (Thiocyanato/Isothiocyanato).
Updated On: Jun 26, 2026
- $OH^-$
- $NH_2^-$
- $I^-$
- $CH_3O^-$
- $CN^-$
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The Correct Option is
Solution and Explanation
Step 1: Understanding the Concept:
A nucleophile that has two or more different atoms through which it can attack a substrate (i.e., multiple nucleophilic centers) is called an ambident nucleophile.
Step 2: Detailed Explanation:
1. Cyanide Ion ($CN^-$): The cyanide ion can act as a nucleophile through either the Carbon atom or the Nitrogen atom.
- Attack through Carbon ($\text{-}C\equiv N$) leads to the formation of nitriles (alkyl cyanides).
- Attack through Nitrogen ($\text{-}N\equiv C$) leads to the formation of isocyanides (isocyanates).
2. Other options like $OH^-$, $I^-$, and $CH_3O^-$ have only one type of atom (Oxygen or Iodine) providing the lone pair for bonding.
Step 3: Final Answer:
$CN^-$ is an ambident nucleophile.
A nucleophile that has two or more different atoms through which it can attack a substrate (i.e., multiple nucleophilic centers) is called an ambident nucleophile.
Step 2: Detailed Explanation:
1. Cyanide Ion ($CN^-$): The cyanide ion can act as a nucleophile through either the Carbon atom or the Nitrogen atom.
- Attack through Carbon ($\text{-}C\equiv N$) leads to the formation of nitriles (alkyl cyanides).
- Attack through Nitrogen ($\text{-}N\equiv C$) leads to the formation of isocyanides (isocyanates).
2. Other options like $OH^-$, $I^-$, and $CH_3O^-$ have only one type of atom (Oxygen or Iodine) providing the lone pair for bonding.
Step 3: Final Answer:
$CN^-$ is an ambident nucleophile.
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