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Chapter 17: Q33P (page 889)

Predict the major products of treating the following compounds with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

(a) isopropylbenzene

(b) p-xylene

(c) tetralin

Short Answer

Expert verified

(a) benzoic acid

(b) terephthalic acid

(c) phthalic acid

Step by step solution

01

Permanganate Oxidation.

Potassium permanganate is a strong oxidizing reagent so it plays a vital role in oxidation.An aromatic ring imparts extra stability to the nearest carbon atom of its side chains. The oxidation induced by KMnO4 is known as permanganate oxidation.

Functional groups such as -NO2 , halogens, -COOH, and -SO3H usually survive this brutal oxidation.

02

Subpart (a) The major products of the reaction of isopropylbenzene.

On reacting isopropylbenzene with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

isopropylbenzene ->benzoic acid

03

Subpart (b) The major products of the reaction of p-xylene.

On reacting p-xylene with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

p-xylene -> terephthalic acid

04

Subpart (c) The major products of the reaction of tetralin.

On reacting tetralin with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

tetralin -> phthalic acid

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Most popular questions from this chapter

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case, it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction

Ephedrine Methamphetamine

Phenolphthalein, 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.

(a) Propose a mechanism for the synthesis of phenolphthalein.

(b) Propose a mechanism for the conversion of phenolphthalein to its red dianion in the 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.


Phthalic anhydride Phenolphthalein red dianion

What products would you expect from the following reactions?

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