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Organic Chemistry

Summary of Reactions

Organic ChemistrySummary of Reactions

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.
    2. Bromination (Section 16.1)
      Benzene reacts with bromine in the presence of iron tribromide to yield bromobenzene and hydrogen bromide.
    3. Chlorination (Section 16.2)
      Benzene reacts with chlorine in the presence of iron trichloride to form chlorobenzene and hydrochloric acid.
    4. Iodination (Section 16.2)
      Benzene reacts with iodine in the presence of copper (2) chloride to form iodobenzene and hydrogen iodide.
    5. Nitration (Section 16.2)
      Benzene reacts with nitric acid in the presence of sulfuric acid to form nitrobenzene and water.
    6. 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.
    7. Friedel–Crafts alkylation (Section 16.3)
      Benzene reacts with methyl chloride in the presence of aluminum trichloride to form methyl benzene and hydrogen chloride.

    8. 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.
  2. 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.
  3. 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.
  4. Oxidation of alkylbenzene side chain (Section 16.8)
    In water, toluene reacts with potassium permanganate to form benzoic acid.
  5. 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.
  6. 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
  7. 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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