Alkaline phenol + chloroethanoic acid

[Kushal]

Homework Statement

chloroethanoic acid is added to an alkaline solution of phenol. Give the structural formula of the organic product formed and state what type of reaction takes place.


it is from a past exam paper and i got no one to check my answer, which I'm a bit unsure of.

The Attempt at a Solution

i believe a displacement reaction occurs. chloroethanoic acid is stronger than phenol. the phenoxide anion(phenol in alkaline solution) will be displaced into phenol, and the ethanoate anion will be formed.

is it that which happens, or another reaction. i don't know if esterification might occur with chloroethanoic acid because it doesn't occur with carboxylic acids.

 

[chemisttree]

Your analysis is correct. Phenoxide ion must be at a pH of roughly 9 or 10 and chloroethanoic acid is a stronger acid (lower pKa) than plain ethanoic acid. Do you know of any base-catalyzed esterification reactions?

Note: this example is not a transesterification reaction...

 

[Kushal]

nopes, i never heard of that?! (yet)

i tried googling a lil bit - no results. what i learned is that phenols are too unreactive for esterification using carboxylic acids.