Question

Please solve this phenol reaction based problem?

Answer 1

Well, it depends on how much excess... If we want to not waste money, then only the top `"OH"` will react... by a thermodynamic factor of about `10^4` over the other one reacting.

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The `"pK"_a` of protonated phenol is about `-6`, and that of protonated ethanol is about `-2.4`. Hence, protonating the top `"OH"` is favored by a factor of `10^(-2.4-(-6))`.

Then we just make the Grignard reagent... provided that the experiment is done properly. Water came off of the protonated alcohol, and must be dried off before reacting with `"Mg"` and dry diethyl ether.