19. Reactions of Aromatics: EAS and Beyond
EAS:Retrosynthesis
2:38 minutes
Problem 17-78
Textbook Question
Textbook QuestionPhenolphthalein, a common nonprescription laxative, is also an acid–base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.
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(b) Propose a mechanism for the conversion of phenolphthalein to its red dianion in base.
(c) Use resonance structures to show that the two phenolic oxygen atoms are equivalent (each with half a negative charge) in the red phenolphthalein dianion.
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