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reaction of benzyl chloride and aqueous NAOH

I was told that benzylchloride doesnt react with hot aqueous NAOH. But , there's one reaction (production of alcohol called DOW process) , in which the benzyl chloride react with NAOH to form C6H5ONa.
I am confused now,. Which is true??

Reply 1

-Rainbow Drops-

Original post by wilson dang

Isn't that phenol and naoh?

Posted from TSR Mobile

Reply 2

GDN

I don't know where you got your info from - benzyl chloride does react with aqueous NaOH to give benzyl alcohol.

The other reaction you mention isn't reasonable since somehow a C to C bond would have to be broken

Reply 3

wilson dang

So the Reaction of benzyl chloride and naoh is feasible??

Reply 4

KombatWombat

Original post by wilson dang

So the Reaction of benzyl chloride and naoh is feasible??

Yes! Might not be as quick as, say, chloroethane but it's perfectly feasible.

Reply 5

wilson dang

Original post by KombatWombat

Yes! Might not be as quick as, say, chloroethane but it's perfectly feasible.

Ok, thanks! :biggrin:

Reply 6

Rithik808

Out of chlorobenzene and benzyl chloride which one gets easily hydrolysed by aq NaOH?

Reply 7

username3718068

Original post by Rithik808

Out of chlorobenzene and benzyl chloride which one gets easily hydrolysed by aq NaOH?

Chlorobenzene won't react with OH- because the delocalised electrons will repel the hydroxide ion so nucleophilic substitution can't occur, which is understandable as the chlorine atom is bonded to the C which as the delocalised pi system.

Benzyl chloride will however undergo the nucleophilic substitution reaction with OH- to produce benzyl alcohol.