← Organic compounds

7 Reaction pathways (interconversions)

Multi-step synthesis questions ask you to get from compound A to compound B. Learn the map. Then any route is just joining arrows. Alkene and haloalkane are the two central “hubs”.

Core interconversions

Alkene H₂O / H⁺ ⟶ Alcohol hydration Alkene HBr ⟶ Haloalkane electrophilic addition Alcohol conc H₂SO₄, Δ ⟶ Alkene dehydration Haloalkane NaOH(aq) ⟶ Alcohol nucleophilic subst. Haloalkane KCN / ethanol ⟶ Nitrile adds a carbon! Haloalkane KOH / ethanol, Δ ⟶ Alkene elimination Nitrile H₂ / Ni ⟶ Amine reduction Nitrile dil. acid, reflux ⟶ Carboxylic acid hydrolysis 1° Alcohol K₂Cr₂O₇/H⁺, distil ⟶ Aldehyde partial oxidation Aldehyde K₂Cr₂O₇/H⁺, reflux ⟶ Carboxylic acid full oxidation Acid + Alcohol conc H₂SO₄ ⟶ Ester esterification ✓

Planning a synthesis

Work backwards from the target. Need to add a carbon? The only chain-lengthening step at L3 is haloalkane → nitrile (KCN). Need an amine? Go via a nitrile or a haloalkane + NH₃. Need a carboxylic acid? Oxidise a 1° alcohol/aldehyde, or hydrolyse a nitrile. Worked example Ethene → ethanoic acid (2 steps + why) Convert CH₂=CH₂ into CH₃COOH. Step 1, hydrate the alkene: CH₂=CH₂ + H₂O (H⁺ catalyst) → CH₃CH₂OH (ethanol). Step 2, fully oxidise the 1° alcohol under reflux: CH₃CH₂OH + K₂Cr₂O₇/H⁺, reflux → CH₃COOH. (Reflux, not distillation: distilling would stop at the aldehyde ethanal.) ✓ Ethene → ethanol (hydration) → ethanoic acid (oxidation, reflux).

Practise just this