Reactions of Aromatic Compounds - McMurry Chapter 16

Flashcards for reviewing key concepts related to electrophilic aromatic substitution and related mechanisms in aromatic chemistry.

Electrophilic aromatic substitution (EAS)

A reaction mechanism involving the substitution of a hydrogen atom on an aromatic ring by an electrophile.

Sigma complex

An intermediate carbocation formed during the electrophilic aromatic substitution, stabilized by resonance.

Nitration

A specific electrophilic aromatic substitution reaction in which a nitronium ion (NO2+) reacts with an aromatic compound.

Halogenation

A reaction where halogen molecules (Br2, Cl2, etc.) react with an aromatic compound in the presence of a Lewis acid catalyst.

Regiochemistry

The study of the preferential direction and position of substitution in electrophilic aromatic substitution reactions.

Inductive effects

Electron density effects transmitted through sigma bonds due to electronegativity differences between atoms.

Resonance effects

The stabilization of a molecule by delocalizing electrons across multiple atoms or bonds.

Activating groups

Substituents that increase the reactivity of an aromatic ring in electrophilic aromatic substitution.

Deactivating groups

Substituents that decrease the reactivity of an aromatic ring in electrophilic aromatic substitution.

Friedel-Crafts alkylation

A type of electrophilic aromatic substitution involving the addition of an alkyl group to an aromatic ring.

Friedel-Crafts acylation

A variation of the Friedel-Crafts reaction that introduces an acyl group to an aromatic ring.

Sandmeyer reaction

A reaction converting aryl amines to aryl halides using diazonium salts.

Benzyne mechanism

A mechanism of nucleophilic aromatic substitution in which a benzyne intermediate is formed through elimination.

Oxidation of aromatic side chains

The transformation of alkyl substituents on aromatic rings into carboxylic acids through oxidation.