Please solve this phenol reaction based problem?

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1 Answer
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 104 over the other one reacting.


The pKa 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 102.4(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.