Benzene reactions

elishamjones
Mind Map by elishamjones, updated more than 1 year ago
elishamjones
Created by elishamjones over 5 years ago
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A level Chemistry Mind Map on Benzene reactions, created by elishamjones on 10/29/2014.

Resource summary

Benzene reactions
1 Electrophilic substitution
1.1 Nitration of Benzene
1.1.1 Electrophile is NO₂⁺
1.1.1.1 Made by protonation of HNO₃ by conc H₂SO₄
1.1.1.1.1 Heated to 50℃
1.1.1.1.2 Makes [H₂NO₃]⁺
1.1.1.1.2.1 Decomposes into NO₂⁺ & H₂O
1.1.1.1.3 H₂SO₄ remade when HSO₄⁻ join H⁺ from the benzene ring
1.1.1.1.3.1 Hence is a cataylst
1.1.2 Dyes
1.1.2.1 Nitrobenzene reduced to Phenylamine

Annotations:

  • By the reduction of a NO₂ group to an NH₂ group using Fe in industry or Sn and strong HCl in a lab
1.1.2.1.1 Phenylamine → Azo dye

Annotations:

  • Phenylamine → Benzenediazonium chloride →  Azo dye.
  • Azo dye contains 2 benzene rings connected by N=N
1.1.3 Explosives
1.1.3.1 Repeat nitration of methylbenzene makes TNT

Annotations:

  • TNT is 2,4,6 trinitromethylbenzene
1.2 Friedal-Crafts acylation
1.2.1 Acyl Chloride + Benzene → Ketone
1.2.1.1 Needs FeCl₂ or AlCl₃ catalyst
1.2.1.1.1 Lewis acids can accept a lone pair of electrons
1.2.1.1.1.1 Lone pair from Chloride on Acyl Chloride
1.2.1.1.1.1.1 Makes an acylium ion
1.2.1.1.1.1.1.1 This is the electrophile
1.2.1.1.2 Will be remade
1.3 A hydrogen is swapped for a functional group
1.4 Benzene delocalised = many electrons
1.4.1 Attacked by electrophiles
1.4.1.1 A species that seeks electrons
1.5 Conditions
1.5.1 High temp
1.5.2 Conc reagents
1.5.3 Catalysts
2 Cannot undergo addition of electrophiles since Benzene is stable
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