Organic 2 Section 3 - Unit 27: Aromatic Chemistry
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Equations for the formation of the electrophile during nitration (2)
• H₂SO₄ + HNO₃ → H₂NO₃+ + HSO₄- - H₂NO₃+2 → H₂O + NO₂+
Reagents and conditions for nitration (3)
• Concentrated nitric acid • Sulfuric acid • Heat
Equations for the formation of the electrophile during Friedel crafts acylation (1)
• R-COCl + AlCl₃ → R-CO+ + AlCl₄-
Reagents and conditions for Friedel crafts acylation (3)
• Acyl chloride - Anhydrous AlCl₃ catalyst
State and explain the stability of benzene compared with the hypothetical cyclohexatriene (4 marks)
• Benzene is more stable than cyclohexatriene • Expected ΔH hydrogenation of C₆H₆ is 3(–120) • Actual ΔH hydrogenation of benzene is 152 kJ mol-1 (less exothermic) • Because of delocalisation / electrons spread out
Give a reagent that could be used in a test-tube reaction to distinguish between benzene and cyclohexene and state the observations (3 marks)
• Bromine • No colour change with benzene • Decolourises with cyclohexene
Give the formula of the reactive intermediate during Friedel crafts acylation (1 mark)
• CH₃CO-
Suggest one reason why phenylamine cannot be prepared from bromobenzene via nucleophilic substitution. Outline a synthesis of phenylamine from benzene, giving only the reagents and conditions for each step (6 marks)
• Benzene ring repels nucleophiles Step 1: • Nitration to form nitrobenzene • Concentrated HNO₃ + concentrated H₂SO₄ • 20-60 degrees Step 2: • Reduction to form phenylamine • Sn/HCl