# Dow's Process for the manufacture of phenol

When chlorobenzene ($\ce{C6H5Cl}$) reacts with aqueous ($\ce{NaOH}$) solution it first forms sodium phenoxide ($\ce{C6H5ONa}$), and then phenol upon reacting with $\ce{H+}$.

But my question is, why can't $\ce{Na}$ directly replace $\ce{Cl}$ from chlorobenzene by breaking $\ce{Na-O}$ bond instead of breaking $\ce{O-H}$ bond?

• You mean the Na from the NaOH? – Simon-Nail-It Mar 5 '16 at 9:15
• Can you clarify what you think the mechanism is for this reaction? I don't quite understand your question. – bon Mar 5 '16 at 13:34
• @Simon-Nail-It Yes sir, Na from NaOH – TheNewGenGamer Mar 5 '16 at 15:19
• So your question is why can't $Na^{+}$ react directly with chlorobenzene instead of reacting with phenol? – Rok Narobe Mar 5 '16 at 15:57
• @RokNarobe No sir, i mean to say that why is the long process used when we can just break the C-Cl bond in benzene and then Na+ can react with Cl to form NaCl and phenyl cation can react with OH- to give phenol. Why is Sodium Phenoxide is being formed before giving phenol ? – TheNewGenGamer Mar 11 '16 at 15:04

The mechanism of this reaction is that $\ce{NaOH}$ being a strong base with some extreme conditions abstracts H from C adjacent to C containing Cl while Cl also leaves.
Subsequent addition of $\ce{NaOH}$ forms the phenoxide ion.