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Reactions and uses of carboxylic acids sheet
5-mark answer frame

Write equations, with reagents and conditions, for: (i) the Hell-Volhard-Zelinsky reaction (ii) decarboxylation (iii) Kolbe electrolysis (iv) esterification (v) the reaction with thionyl chloride.

How to lay out the answer. Follow the frame, then write it in your own words.

  1. 1 · HVZ reaction. CH₃COOH → (i) Cl₂, red phosphorus (ii) H₂O → ClCH₂COOH; the α-hydrogen is replaced.
  2. 2 · Decarboxylation. CH₃COONa + NaOH → (CaO, heat) CH₄ + Na₂CO₃; soda lime; one carbon fewer.
  3. 3 · Kolbe electrolysis. 2CH₃COONa + 2H₂O → (electrolysis) CH₃CH₃ + 2CO₂ + H₂ + 2NaOH.
  4. 4 · Esterification. CH₃COOH + C₂H₅OH ⇌ (conc. H₂SO₄) CH₃COOC₂H₅ + H₂O; reversible, so water is removed.
  5. 5 · Thionyl chloride. RCOOH + SOCl₂ → RCOCl + SO₂ + HCl; gaseous by-products escape.
  6. 6 · Link to real life. Esters made this way give the fruity smells used in perfumes and flavours.
  7. 7 · Close in one line. So the same -COOH group can be halogenated, removed, doubled up or turned into derivatives.

Scoring tip: Name each reaction before you write it, and write the catalyst or condition (red P, CaO, electrolysis, conc. H₂SO₄) on the arrow.