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Discussion

The reaction through which 4-mrthaoxyacetophenone is converted to 4-methoxybenzoic acid is a haloform reaction. This reaction involves two distinct stages that occur in the same environment. The first stage occurs through the based-catalyzed halogenation of the ketone that forms a trihalo ketone. First, the bleach is transformed into chlorine and hydroxide ions through the following reaction:


Then, the hydroxyl is able to attack the rather acidic (pKa ~ 20) α-hydrogen of the ketone. This acidity is due to the stability of the resonance structures of the corresponding enolate ion that forms upon dissociation. When the hydroxide is able to subtract a hydrogen atom, a carbanion is formed. This carbanion is a very strong base and is able to attack the chlorine thus taking one of the chlorine atoms. The introduction of one chlorine atom catalyzes the attack of another hydroxide molecule on the remaining α-hydrogens of the ketone. The subsequent attacks occur faster......

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