Organic Chemistry

Cycloheptatrienyl bromide is an ionic compound because its cation is aromatic. The alkyl halide is notaromatic in the covalent f ...

602 CHAPTER 15 Aromaticity • Reactions of Benzene 15.5 Antiaromaticity An aromatic compound is more stablethan an analogous cycl ...

Section 15.6 A Molecular Orbital Description of Aromaticity and Antiaromaticity 603 Energy Energy nonbonding MOs a. b. d. antibo ...

604 CHAPTER 15 Aromaticity • Reactions of Benzene 15.7 Nomenclature of Monosubstituted Benzenes Some monosubstituted benzenes ar ...

Section 15.8 How Benzene Reacts 605 THE TOXICITY OF BENZENE Although benzene has been widely used in chem- ical synthesis and ha ...

The reaction coordinate diagram in Figure 15.4 shows that the reaction of benzene to form a substituted benzenehas a close to ze ...

Section 15.9 General Mechanism for Electrophilic Aromatic Substitution Reactions 607 In an electrophilic aromatic substitution r ...

608 CHAPTER 15 Aromaticity • Reactions of Benzene 15.10 Halogenation of Benzene The bromination or chlorination of benzene requi ...

Section 15.11 Nitration of Benzene 609 THYROXINE Thyroxine is a hormone that regulates the meta- bolic rate, causing an increase ...

nitric acid N O HO O− nitronium ion OON + + 610 CHAPTER 15 Aromaticity • Reactions of Benzene To generate the necessary electrop ...

Section 15.12 Sulfonation of Benzene 611 Sulfonation of benzene is a reversible reaction. If benzenesulfonic acid is heated in d ...

James Mason Crafts (1839–1917) was born in Boston, the son a of woolen-goods manufacturer. He graduated from Harvard in 1858 and ...

PROBLEM 21 Propose a mechanism for the following reaction: The synthesis of benzaldehyde from benzene poses a problem because fo ...

614 CHAPTER 15 Aromaticity • Reactions of Benzene INCIPIENT PRIMARY CARBOCATIONS For simplicity, we have shown the formation of ...

Section 15.15 Alkylation of Benzene by Acylation–Reduction 615 PROBLEM 22 Show the mechanism for alkylation of benzene by an alk ...

Besides avoiding carbocation rearrangements, another advantage of preparing alkyl- substituted benzenes by acylation–reduction r ...

Summary 617 The Suzuki reactioncouples an aryl halide with an organoborane. The required organoborane is obtained from the react ...

618 CHAPTER 15 Aromaticity • Reactions of Benzene Summary of Reactions Electrophilic aromatic substitution reactions: a. Haloge ...

g.Alkylation via a Suzuki reaction (Section 15.15) Clemmensen reduction and Wolff–Kishner reduction (Section 15.15) CR O CR O ...

620 CHAPTER 15 Aromaticity • Reactions of Benzene Which ion in each of the following pairs is more stable? Which can lose a pro ...