Arenes
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What type of reaction is characteristic of arenes, and why?
Arenes undergo electrophilic substitution reactions due to the delocalized π-electron system (aromatic stabilization). Addition reactions would disrupt the stable delocalized system, requiring more energy.
Describe the mechanism for the nitration of benzene.
1. Formation of electrophile: HNO₃ + H₂SO₄ → NO₂⁺ + HSO₄⁻ + H₂O. 2. Electrophilic attack: NO₂⁺ attacks benzene ring, forming a carbocation intermediate. 3. Deprotonation: HSO₄⁻ removes a proton, regenerating the benzene ring and forming nitrobenzene.
What are the reagents and conditions for the complete oxidation of a side-chain on an arene?
Hot alkaline KMnO₄ followed by dilute acid. This oxidizes the alkyl group to a carboxyl group, forming a benzoic acid derivative.
What catalyst is required for the halogenation of benzene, and what is its role?
A Lewis acid catalyst such as AlCl₃ or AlBr₃ is required. It polarizes the halogen molecule (
Describe the Friedel-Crafts alkylation reaction.
It involves reacting an arene with an alkyl halide (
What product is formed when benzene is hydrogenated using H₂ and a Pt/Ni catalyst with heat?
Cyclohexane (C₆H₁₂). The benzene ring is saturated with hydrogen atoms, converting the aromatic ring into a saturated cyclic alkane.
Explain how substituents on a benzene ring can affect the position of further electrophilic substitution.
Substituents direct incoming groups to specific positions. Electron-donating groups (
Under what conditions will halogenation occur in the side-chain of an arene, rather than on the aromatic ring?
Halogenation of the side-chain occurs under UV light or high temperatures without a Lewis acid catalyst. This promotes free radical substitution in the alkyl side-chain.
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