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Benzene

AQA A-level chemistry aromatic chemistry year 13

TermDefinition
Why benzene is so stable and how to break it Has a perfect ring of delocalised electrons making it difficult to attack. In order to attack it, it must be by electrophilic addition but only a very powerful electrophile will work
Electrophilic substitution: nitration Substituting a nitrate (NO2+) ion into a benzene ring, used in dyes and explosives. Produced by heating benzene with conc. sulphuric and nitric acid
Reactions for nitrating mix H2SO4(aq) + HNO3(aq) - H2NO3+(aq) + HSO4-(aq) H2NO3-(aq) + H2SO4(aq) - NO2+(aq) + H3O+(aq) + HSO4-(aq)
Conditions for reaction Temperature shouldn’t rise above 55*C otherwise there will be multiple nitration on the benzene ring which can be explosive, especially since the reaction is exothermic
Electrophilic substitution: Friedel-Crafts acylation Benzene is used in pharmaceuticals so it is turned into aromatic ketones to make it easier to use. In order to make an aromatic ketone, an acyl chloride with an aluminium chloride catalyst (halogen carrier) to produce a much stronger acyl electrophile
Halogen carrier A compound capable of transporting halogen atoms temporarily in a chemical reaction
Reaction for acyl ions and catalyst regeneration AlCl3(aq) + COClR(aq) - AlCl4-(aq) + C+OR(aq) AlCl4-(aq) + H+(aq) - AlCl3(aq) + HCl(aq)
Created by: Study_B
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