Question

Can we use nucleophiles such as NH₃, CH₃O for the Nucleophilic substitution of alcohols?

Answer 1

1. Increasing order of nucleophilicity,

NH₃ < –OH^⊕ < CH₃O^⊖

2. Higher electron density will increase nucleophilicity.

3. Negatively charged species are almost always more nucleophiles than neutral species.

4. RO^⊖ has an alkyl group attached, allowing a greater amount of polarizability. This means oxygen’s lone pairs will be more readily available to reach in RO^⊖ than in OH^⊖. Hence CH₃O^– is the better nucleophile for the nucleophilic substitution of alcohols. NH₃ cannot act as a nucleophile for the nucleophilic substitution of alcohols.