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Aromatic Chemistry

ISBN: 978-0-471-54931-4
168 pages
December 2003
Aromatic Chemistry (0471549312) cover image
This book provides an up-to-date and comprehensive account of aromatic chemistry. A series of chapters describes the synthesis and reactions of the major functional derivatives of benzene and the more common polycyclic systems. The concepts of aromaticity and the mechanism of aromatic substitution are discussed, as is the use of metals in the synthesis of aromatic compounds. Throughout, emphasis is placed on mechanisms. Worked problems and questions are provided to aid understanding.

In addition to providing material required by an undergraduate studying chemistry, Aromatic Chemistry is also ideal for industrial chemists seeking to update their knowledge of this important aspect of chemistry.

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1. Aromaticity.

1.1 Introduction.

1.2 Structure of Benzene.

1.3 Stability of the Benzene Ring.

1.4 The Hückel Rule.

1.5 Nomenclature.

2. Aromatic Substitution.

2.1 Introduction.

2.2 Electrophilic Aromatic Substituion (S<sub>E</sub>Ar).

2.3 Reactivity and Orientation in Electrophilic Aromatic Substitution.

2.4 The Hammett Equation.

2.5 Nucleophilic Aromatic Substitution.

2.6 ipso Substitution.

3. Alkylbenzenes and Arylbenzenes.

3.1 Introduction.

3.2 Source of Alkylbenzenes.

3.3 Introduction of Alkyl Groups.

3.4 Reactions of Alkylbenzenes.

3.5 Aryl Derivatives of Benzene.

4. Phenols.

4.1 Introduction.

4.2 Industrial Synthetic Methods.

4.3 Laboratory Syntheses.

4.4 The Acidity of Phenols.

4.5 Reactions of the Hydroxy Group.

4.6 Reactions of the Ring.

4.7 Dihydroxybensenes.

5. Aromatic Acids.

5.1 Introduction.

5.2 Introduction of Acidic Groups.

5.3 Reactions of Aromatic Acids.

5.4 Acidity of Aromatic Acids.

5.5 Compounds with More Than One Acidic Group.

5.6 Side-chain Acids.

6. Aromatic Aldehydes, Ketones and Alcohols.

6.1 Introduction.

6.2 Aromatic Alcohols.

6.3 Aromatic Aldehydes.

6.4 Aromatic Ketones.

7. Nitro Compounds.

7.1 Introduction.

7.2 Introduction of the Nitro Group.

7.3 Charge Transfer Complexes.

7.4 Reactions of Nitro Compounds.

7.5 Nitrosobenzene and Phenylhydroxylamine.

8. Aromatic Amines and Diazonium Salts.

8.1 Introduction.

8.2 Introduction of the amino Group.

8.3 Reactions of Aromatic Amines.

8.4 Related Compounds.

8.5 Basicity Of Amines.

8.6 Diazonium Salts.

9. Aromatic Halogen Compounds.

9.1 Introduction.

9.2 Synthesis of Aryl Halides.

9.3 Reactions of Aryl Halides.

9.4 Aromatic Halogen Compounds Substituted in the Aide Chain.

10. Organometallic Reactions.

10.1 Grignard and Organolithium Reagents.

10.2 Electrophilic Metallation.

10.3 Transition Metal Mediated Processes.

10.4 Aryl Coupling Reactions.

10.5 Arene-Chromium Tricarbonyl Complexes.

11. Oxidation and Reduction of Aromatic Compounds.

11.1 Introduction.

11.2 Reduction of the Benzene Ring.

11.3 Oxidation of the Benzene Ring.

12. Polycyclic Aromatic Hydrocarbons.

12.1 Introduction.

12.2 Chemistry of Naphthalene.

12.3 Chemistry of Anthracene.

12.4 Chemistry of Phenanthrene.

Further Reading.

Answers to Problems.

Subject Index.

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John D. Hepworth is Professor at the University of Central Lancashire.

David R. Waring is formerly of Kodak, Ltd., in Kirkby, Liverpool.

Michael J. Waring is employed by AstraZeneca in Alderley Park, Chesire.

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