Question

Among the following, the ambident nucleophile is

• A. iodide
• B. alkoxy
• C. hydroxyl
• D. hydride
• E. cyanide

Hint:

Ambident nucleophiles have two donor atoms. Example: \(CN^-\), \(NO_2^-\).

Answer 1

Answer: (E)

Concept: An ambident nucleophile is a nucleophile that has two different atoms through which it can donate electron pairs. This means it can attack an electrophile via two different sites.

Step 1: Understanding nucleophiles.
A nucleophile is a species having a lone pair of electrons which it donates to an electrophile.

Step 2: Check each option carefully.
• Iodide (\(I^-\)) → only iodine donates electrons → single site → not ambident
• Alkoxy (\(RO^-\)) → oxygen donates electrons → single site
• Hydroxyl (\(OH^-\)) → only oxygen → single site
• Hydride (\(H^-\)) → only hydrogen → single site
• Cyanide (\(CN^-\)) → can attack via:
• Carbon atom (forms nitriles)
• Nitrogen atom (forms isonitriles)

Step 3: Conclusion.
Since cyanide has two reactive centers, it is an ambident nucleophile. \[ \boxed{\text{Cyanide is ambident nucleophile}} \]