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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