Question

Phenol does not undergo nucleophilic substitution reaction easily due to ______.

Options

• acidic nature of phenol

• partial double bond character of C-OH bond

• partial double bond character of C-C bond

• instability of phenoxide ion

Answer 1

Phenol does not undergo nucleophilic substitution reaction easily due to partial double bond character of C-OH bond.

Explanation:

The lone pair on oxygen is delocalized into the aromatic ring (resonance), giving the C–O bond partial double‑bond character and making it stronger; consequently, –OH is a poor leaving group and nucleophilic substitution is difficult.