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16.15: Summary of Reactions

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    459823
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    16 • Summary of Reactions 16 • Summary of Reactions
    1. Electrophilic aromatic substitution
      1. Fluorination (Section 16.2)
        Benzene reacts with a fluorinating agent to form fluorobenzene.
    • Bromination (Section 16.1)
      Benzene reacts with bromine in the presence of iron tribromide to yield bromobenzene and hydrogen bromide.
    • Chlorination (Section 16.2)
      Benzene reacts with chlorine in the presence of iron trichloride to form chlorobenzene and hydrochloric acid.
    • Iodination (Section 16.2)
      Benzene reacts with iodine in the presence of copper (2) chloride to form iodobenzene and hydrogen iodide.
    • Nitration (Section 16.2)
      Benzene reacts with nitric acid in the presence of sulfuric acid to form nitrobenzene and water.
    • Sulfonation (Section 16.2)
      Benzene reacts with sulfur trioxide in the presence of sulfuric acid to form benzene bonded to S O 3 H group.
    • Friedel–Crafts alkylation (Section 16.3)
      Benzene reacts with methyl chloride in the presence of aluminum trichloride to form methyl benzene and hydrogen chloride.
    • Friedel–Crafts acylation (Section 16.3)
      Benzene reacts with acetyl chloride in the presence of aluminum trichloride to form benzene bonded to an acetyl group and hydrogen chloride.
    • Reduction of aromatic nitro groups (Section 16.2)
      Nitrobenzene reacts with iron in the presence of acid in step 1, and base in step 2 to form a benzene ring bonded to an amino group.
    • Nucleophilic aromatic substitution
      1. By addition to activated aryl halides (Section 16.6)
        Benzene with three nitro groups and a chlorine atom reacts with sodium hydroxide to form benzene with three nitro groups and a hydroxyl group.
      2. By formation of benzyne intermediate from unactivated aryl halide (Section 16.7)
        Bromobenzene reacts with sodium amide in the presence of ammonia to form aniline and sodium bromide.
    • Oxidation of alkylbenzene side chain (Section 16.8)
      In water, toluene reacts with potassium permanganate to form benzoic acid.
    • Benzylic bromination of alkylbenzene side chain (Section 16.8)
      In C C l 4, toluene reacts with N-bromosuccinimide in the presence of benzyl peroxide to form benzene bonded toa C h 2 B r group.
    • Catalytic hydrogenation of aromatic ring (Section 16.9)
      Benzene reacts with hydrogen to form cyclohexane.in the presence of rhodium on carbon as a catalyst
    • Reduction of aryl alkyl ketones (Section 16.9)
      A carbonyl group bonded to a benzene ring on one side and an R groyp on the other reacts with hydrogen in the presence of palladium to form benzene bonded to a C H 2 R group.

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