1559T_ch22_389-40810/19/0517:23Pa9e389 EQA 22 Chemistry of Benzene Substituents: Alkylbenzenes,Phenols,and Benzenamines atonr to a benzene nng (a benzy zene ring with the attached groups modifies their chemistry significantly. Outline of the Chapter 21-1 Benzylic Resonance Stabilization Carbons attached to benzene rings display enhanced reactivity 22-2 Benzylic Oxidations and Reductions Including one especially useful oxidation of alkyl side chains. 22-3 Naming and Properties of Phenols 22-4 Preparation of Phenols:Nucleophilic Aromatic Substitution Useful new methods for synthesizing benzene derivatives 22-5 Alcohol Chemistry of Phenols 22-6 Electrophilic Substitution of Phenols 22-7 Claisen and Cope Rearrangements 22-8 Oxidation of Phenols:Benzoquinones Aromatic alcohols:how the functional groups affect one another 22-9 Oxidation-Reduction Processes in Nature 22-10,22-11 Arenediazonium Salts and Diazo Coupling Using aromatic amines to synthesize substituted benzenes Keys to the Chapter 22-1.Benzylic Resonance Stabilization go back andtaethe ffor the perolmethl (ben nion.There are I forms for each one.lea stability and ase of formation. 389 22 Chemistry of Benzene Substituents: Alkylbenzenes, Phenols, and Benzenamines In this chapter you continue to study the chemistry of aromatic compounds. You find out about reactions at a carbon attached to a benzene ring (a “benzylic” carbon) and about more transformations of benzenes contain￾ing either hydroxy or amino groups connected directly to the ring. In all these cases the interaction of the ben￾zene ring with the attached groups modifies their chemistry significantly. Outline of the Chapter 21-1 Benzylic Resonance Stabilization Carbons attached to benzene rings display enhanced reactivity. 22-2 Benzylic Oxidations and Reductions Including one especially useful oxidation of alkyl side chains. 22-3 Naming and Properties of Phenols 22-4 Preparation of Phenols: Nucleophilic Aromatic Substitution Useful new methods for synthesizing benzene derivatives. 22-5 Alcohol Chemistry of Phenols 22-6 Electrophilic Substitution of Phenols 22-7 Claisen and Cope Rearrangements 22-8 Oxidation of Phenols: Benzoquinones Aromatic alcohols: how the functional groups affect one another. 22-9 Oxidation–Reduction Processes in Nature 22-10, 22-11 Arenediazonium Salts and Diazo Coupling Using aromatic amines to synthesize substituted benzenes. Keys to the Chapter 22-1. Benzylic Resonance Stabilization Chemical reactivity at a saturated carbon atom attached to a benzene ring is greatly enhanced over that of or￾dinary alkyl carbons. Delocalization stabilizes both reaction transition states and intermediates. After reading this section once, go back and take a good look at the sets of resonance forms for the phenylmethyl (benzyl) radical, cation, and anion. There are four forms for each one, leading to increased stability and ease of formation. 389 1559T_ch22_389-408 10/19/05 17:23 Page 389