Organic Synthesis

2026 Syllabus Objectives

By the end of this topic, you should be able to:

  1. For an organic molecule containing several functional groups:

    • (a) Identify organic functional groups using the reactions in the syllabus
    • (b) Predict properties and reactions
  2. Devise multi-step synthetic routes for preparing organic molecules using the reactions in the syllabus

  3. Analyse a given synthetic route in terms of type of reaction and reagents used for each step of it, and possible by-products


1. Identifying Functional Groups

A functional group is a specific group of atoms in a molecule that determines how that molecule behaves in chemical reactions. Think of it like the "active part" of the molecule that does the chemistry.

When you have a molecule with several functional groups, you need to be able to spot each one and predict what reactions it can undergo.

Functional Groups: How to Identify and Make Them

Here's a summary of the main functional groups you need to know:

Alkanes

  • Test: No specific chemical test available
  • How to make them:
    • Add hydrogen (H₂) to alkenes using a Pt or Ni catalyst with heat (this is called hydrogenation)
    • Break down crude oil using heat and an Al₂O₃ catalyst (called cracking)

Alkenes

  • Test: They turn bromine water from orange to colourless (we say they "decolourise" bromine water)
  • How to make them:
    • Heat halogenoalkanes with ethanolic NaOH (this removes a small molecule, called elimination)
    • Remove water from alcohols using a hot Al₂O₃ catalyst (called dehydration)
    • Crack crude oil using heat and Al₂O₃ catalyst

Halogenoalkanes (primary, secondary, and tertiary)

  • Test: Add dilute nitric acid, then silver nitrate, then dilute ammonia solution. You'll see a coloured precipitate:
    • AgCl = white precipitate
    • AgBr = cream precipitate
    • AgI = yellow precipitate
  • How to make them:
    • React alkanes with halogens under UV light (free-radical substitution)
    • Add hydrogen halides (like HBr) to alkenes (electrophilic addition)
    • React alcohols with reagents like HX gas, or KCl with concentrated H₂SO₄, or PCl₃ with heat, or PCl₅, or SOCl₂ (nucleophilic substitution)

Alcohols (primary, secondary, and tertiary)

  • Tests: Several ways to identify alcohols:
    • React with carboxylic acid and sulfuric acid to make esters (these smell fruity)
    • Primary alcohols can be oxidised to aldehydes (which give positive tests with Fehling's and Tollens' solution) and then to carboxylic acids
    • Secondary alcohols can be oxidised to ketones (positive test with 2,4-DNPH but NOT with Fehling's or Tollens')
    • Tertiary alcohols cannot be oxidised at all
  • How to make them:
    • Add steam to alkenes using concentrated phosphoric(VI) acid as catalyst (electrophilic addition)
    • Oxidise alkenes with cold, dilute KMnO₄ to form a diol (a molecule with two OH groups)
    • Heat halogenoalkanes with NaOH(aq) (nucleophilic substitution)
    • Reduce aldehydes or ketones using NaBH₄ or LiAlH₄ (aldehydes → primary alcohols; ketones → secondary alcohols)
    • Reduce carboxylic acids using LiAlH₄
    • Break down esters using dilute acid or dilute alkali (hydrolysis)

Aldehydes

  • Tests:
    • Forms a silver mirror with Tollens' reagent
    • Forms a red precipitate with Fehling's solution
    • Forms an orange precipitate with 2,4-DNPH
  • How to make them:
    • Oxidise primary alcohols using acidified K₂Cr₂O₇ or KMnO₄, with distillation to stop the aldehyde oxidising further into a carboxylic acid

Ketones

  • Test: Forms an orange precipitate with 2,4-DNPH (but does NOT react with Fehling's or Tollens')
  • How to make them:
    • Oxidise secondary alcohols using acidified K₂Cr₂O₇ or KMnO₄ under distillation

Carboxylic Acids

  • Test: React with carbonates to produce CO₂ gas, which turns limewater cloudy
  • How to make them:
    • Oxidise aldehydes and primary alcohols using acidified K₂Cr₂O₇ or KMnO₄ under reflux (heating with a condenser so nothing escapes)
    • Break down nitriles using dilute acid or dilute alkali, then add acid (hydrolysis)
    • Break down esters using dilute acid or dilute alkali, then add acid (hydrolysis)

Esters

  • Test: Have sweet, fruity smells
  • How to make them:
    • React alcohols with carboxylic acids using hot, concentrated H₂SO₄ as catalyst (this is a condensation reaction because a small molecule—water—is eliminated)

Amines

  • Tests:
    • Turn damp red litmus paper blue
    • Turn universal indicator blue/purple
  • How to make them:
    • Heat halogenoalkanes under pressure with ammonia (NH₃) in ethanol (nucleophilic substitution)

Nitriles

  • Test: No official test
  • How to make them:
    • Heat halogenoalkanes under pressure with KCN in ethanol (nucleophilic substitution)

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