Log out Go to App
Go to App

Learning Materials

Features

Discover

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

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Question: When benzene is treated with D2SO4, deuterium slowly replaces all six hydrogens in the aromatic ring. Explain.

The compound MON-0585 is a nontoxic, biodegradable larvicide thatis highly selective against mosquito larvae. Synthesize MON-0585 using either benzene or phenol as a source of the aromatic rings.

The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy conformation of the molecule. Why are the two benzene rings tilted at a 63° angle to each other rather than being in the same plane so that their p orbitals overlap? Why doesn’t complete rotation around the single bond joining the two rings occur?

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

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

Recommended explanations on Chemistry Textbooks

Nuclear Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

Kinetics

Read Explanation

Chemical Analysis

Read Explanation

Chemistry Branches

Read Explanation

Chemical Reactions

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free