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Chapter 16: Q29E (page 524)

The sulfonation of an aromatic ring with is reversible. That is, heating benzenesulfonic acid with H2SO4 yields benzene. Show the mechanism of the desulfonation reaction. What is the electrophile?

Short Answer

Expert verified

It is a process of the addition of the sulphonic group in the presence of sulphuric acid it occurs by the removal of the one hydrogen from the sulphuric acid and addition of SO3H to the benzene ring.

Step by step solution

01

Step-by-Step SolutionStep 1:  Sulphonation

It is a process of the addition of the sulphonic group in the presence of sulphuric acid it occurs by the removal of the one hydrogen from the sulphuric acid and addition of SO3H to the benzene ring.

02

De- Sulphonation

It lead to removal of the sulphonic group by deportation and also leads to the regaining of aromaticity, again and again, benzene ring formation occurs.

03

Electrophile

Proton is the electrophile here having protons that are electropositive in nature.

04

Reaction occurs as

  1. Sulphonation
  2. De Sulphonation


Sulphonation and De-Sulphonation

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Most popular questions from this chapter

Question: Would you expect p-methyl phenol to be more acidic or less acidic than unsubstituted phenol? Explain. (See Problem 16-75.)

At what position would you expect electrophilic substitution to occur in each of the following substances?

a.

b.

c.

Propose a mechanism to account for the reaction of benzene with 2,2,5,5-tetramethyltetrahydrofuran.

How many products might be formed on chlorination of o-xylene (o-dimethylbenzene), m-xylene, and p-xylene?

Question: Phenols (ArOH) are relatively acidic, and the presence of a substituent group on the aromatic ring has a large effect. Thepka of unsubstituted phenol, for example, is 9.89, while that of p-nitrophenol is 7.15. Draw resonance structures of the corresponding phenoxide anions and explain the data.
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