MCAT Organic Chemistry Review 2018-2019

(singke) #1
using   strong  acid,   the resultant   product is  the same    as  the initial reactant.   Neither of  the
oxidation products in choices (B) or (C), nor the reduction product in choice (D), will be formed.

11 . A
This reaction will create a ketal. This is the first step of the protection of aldehydes or ketones
using dialcohols.


12 . D
This is the Jones oxidation, which will convert a primary alcohol into a carboxylic acid. Choice (A)
is the original reacting molecule, and because the reaction will proceed, this is not correct.
Because the reaction uses strong oxidizing agents, it won’t stop at the aldehyde, choice (B). This
reaction also cannot make the ketone in choice (C) because it starts with a primary alcohol.


13 . B
In order to convert phenols into hydroxyquinones, they must first be converted to quinones
through an oxidation step; a second oxidation step is required to further oxidize quinones to
hydroxyquinones.


14 . C
The reaction that converts ubiquinone into ubiquinol is a reduction reaction in which two
ketones are reduced to two hydroxyl groups.


15 . A
An acetal can be converted to a carbonyl and a dialcohol by treatment with aqueous acid. This is
the final step when using alcohols as protecting groups, called deprotection.

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