Question

Example of an ambident nucleophile is

• A. Iodide
• B. Water
• C. Hydroxyl ion
• D. Cyanide

Answer 1

The Correct Option is D

To determine which of the given options is an ambident nucleophile, we need to understand the concept of ambident nucleophiles and analyze each option.

1. Understanding Ambident Nucleophiles:
An ambident nucleophile is a species that has two or more nucleophilic sites (atoms with lone pairs) that can attack an electrophile. These sites are usually connected through resonance or tautomerism.

2. Analyzing Each Option:
a) Iodide (I⁻):
- Has only one nucleophilic site (the iodine atom) - Not ambident

b) Water (H₂O):
- Has lone pairs on oxygen but no alternative nucleophilic site - Not ambident

c) Hydroxyl ion (OH⁻):
- Has lone pairs only on oxygen - Not ambident

d) Cyanide (CN⁻):
- Has two nucleophilic sites: carbon and nitrogen - Can attack through either atom (resonance stabilized) - Classic example of ambident nucleophile

3. Why Cyanide is Ambident:
The cyanide ion can participate in reactions through either:
- Carbon atom (forming alkyl cyanides)
- Nitrogen atom (forming isocyanides)
This dual reactivity makes it ambident.

4. Key Characteristics of Ambident Nucleophiles:
- Must have multiple nucleophilic centers
- The centers must be connected through conjugation or resonance
- Should be able to form different products depending on attack site

Final Answer:
The example of an ambident nucleophile from the given options is cyanide (CN⁻).