Please solve this phenol reaction based problem?

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1 Answer
Truong-Son N.
Mar 25, 2018

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.

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.

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