Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 16, Problem 16.53AP
Interpretation Introduction

Interpretation:

The curved-arrow mechanism for the conversion of benzenesulfonic acid into benzene and H2SO4 with hot water is to be predicted.

Concept introduction:

The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by another electrophile is known as electrophilic aromatic substitution reaction. Some electrophilic aromatic substitution reactions are reversible in nature they convert back the product electrophilic aromatic substitution reactions into its reactant.

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Complete the electrophilic aromatic substitution mechanisms with the necessary substances!
a) Put these three common types of carbonyl compound in order of decreasing reactivity         ester          amide          acid chloride           b) For the least reactive, show the interconversion to its other resonance form:         How does this electron delocalisation make it stable?         c) For the most reactive, draw the mechanism of its undergoing hydrolysis (reaction with H2O): Why makes this type of carbonyl so reactive to nucleophiles?
Indicate the following statement as true/false. Some of the groups pre-bonded to an aromatic ring cause electrophilic aromatic substitution to occur mainly at the ortho and para sites. Others lead to the meta location. RightFalse

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