Halogenoarenes, also known as aryl halides, are aromatic compounds with halogen atoms replacing hydrogen in an arene like benzene. They are synthesized through electrophilic aromatic halogenation and the Sandmeyer reaction. Despite their limited reactivity in nucleophilic aromatic substitution due to the aromatic ring's stability, they can form Grignard reagents and undergo substitution with strong electron-withdrawing groups. Their hydrolysis reactivity is lower compared to acyl and alkyl chlorides, attributed to the resonance-stabilized carbon-halogen bond.
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Halogenoarenes are aromatic compounds where one or more hydrogen atoms of an arene have been replaced by halogen atoms
Delocalized π-electron system
Benzene has a delocalized π-electron system over the ring, contributing to its stability and unique reactivity
Alternating double and single bonds
The structural formula of benzene is characterized by alternating double and single bonds
Halogenoarenes are synthesized through methods such as electrophilic aromatic halogenation and the Sandmeyer reaction
Electrophilic aromatic halogenation is a substitution reaction where a halogen is introduced to the benzene ring using a Lewis acid catalyst
The Sandmeyer reaction converts aniline derivatives to aryl halides via diazonium salts
Halogenoarenes can be used to generate Grignard reagents, such as phenylmagnesium bromide, by reacting with magnesium in dry ether
Halogenoarenes can undergo nucleophilic aromatic substitution when strong electron-withdrawing groups are present on the ring
The hydrolysis of halides is influenced by the nature of the carbon-halogen bond, with acyl chlorides being the most reactive and aryl chlorides being the least reactive
Halogenoarenes are essential in the field of chemical manufacturing, used to substitute a hydrogen atom in an aromatic ring with a halogen
Halogenoarenes are used to synthesize a wide array of products, including pharmaceuticals, agrochemicals, and materials for advanced technologies
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Benzene, a molecule with a ring of six carbon atoms, is symbolized by C6H6 and is known for its ______ π-electron system.
delocalized
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Electrophilic aromatic halogenation catalysts
Iron(III) chloride or aluminum chloride used to facilitate halogen introduction to benzene ring.
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Sandmeyer reaction starting material
Aniline derivatives treated with nitrous acid to form diazonium salts for aryl halide synthesis.
