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

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?

At what position and on what ring do you expect nitration of 4-bromobiphenyl to occur? Explain, using resonance structures of the potentialintermediates.

How would you prepare diphenylmethane, (Ph)2CH2 , from benzene and an acid chloride?

How would you synthesize the following substances starting from benzene or phenol? Assume that ortho- and para-substitution products can

be separated.

(a)o-Bromobenzoic acid (b)p-Methoxytoluene

(c)2,4,6-Trinitrobenzoic acid (d)m-Bromoaniline

Addition of HBr to 1-phenylpropene yields only (1-bromopropyl) benzene. Propose a mechanism for the reaction, and explain why none of the other regioisomer is produced.
See all solutions

Recommended explanations on Chemistry Textbooks

The Earths Atmosphere

Read Explanation

Physical Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Organic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Chemical Analysis

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