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