Reactions of Aromatic Compounds

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Nitration of Benzene Benzene reacts only slowly with hot concentrated nitric acid to give nitrobenzene. The reaction is much faster in a mixture of concentrated nitric acid (pK a = -1.4) and concentrated sulfuric acid, a much stronger acid (pK a = -9). + HNO 3 + H 2SO 4 Concentrated acids ~ 50 o C NO 2 + H 3O + + HSO 4 - Nitrobenzene (~ 85%)
Mechanism of Nitration (1) Generation of the Electrophile Nitric acid undergoes reversible dehydration in the presence of concentrated sulfuric acid producing the nitronium ion, a strong electrophile. H-O : : : O: N + = pK a = -1.4 + H-O H : O: - : : : O: N + = O: - : : + H-OSO 3H pK a = -9 H 2O + + H-O H : : O: N : O: : O: N = + = + = Nitronium ion O: - : : + -OSO3H
Page 1 and 2: Chapter 15 Reactions of Aromatic Co
Page 3 and 4: Examples of Electrophilic Aromatic
Page 5 and 6: Step 2: Deprotonation of the Areniu
Page 7 and 8: Halogenation of Benzene Halogenatio
Page 9 and 10: Mechanism: Step 1: Electrophilic At
Page 11: Iodination of Benzene Direct iodina
Page 15 and 16: Sulfonation of Benzene Benzene reac
Page 17 and 18: (4) Acid-Base Equilibrium :O: S O:
Page 19 and 20: A Mechanism for the Alkylation Reac
Page 21 and 22: Evidence for Carbocation Intermedia
Page 23: 2) Alcohols alkylate arenes in the

Reactions of Aromatic Compounds

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