Alcohol classification and the reactions of alcohols and phenol

ChemistryOrganic ChemistryAges 16–17

Use with my class

Choose ethanol (primary), propan-2-ol (secondary), 2-methylpropan-2-ol (tertiary) or phenol: the simulation draws the structural formula, highlights the –OH group and counts the carbons attached to the carbon bearing –OH to fix its class. Pick a reagent (Na, CuO with heat, concentrated H₂SO₄, bromine water, NaOH solution) and press Run: the test tube shows the correct outcome — H₂ bubbles, a white 2,4,6-tribromophenol precipitate, red copper metal, or no reaction — together with the equation and temperature conditions.

Lesson: Alcohols: classification, substitution of the –OH hydrogen, dehydration, oxidation; phenol and its reactions with bromine water and NaOH

What it shows

Alcohols are classified as primary, secondary or tertiary by counting the carbon atoms bonded to the carbon that carries the –OH group. The class decides how they react: primary alcohols are oxidised to aldehydes and secondary alcohols to ketones, while tertiary alcohols resist oxidation because that carbon has no hydrogen to lose. In phenol the –OH group is attached directly to a benzene ring, so phenol is a weak acid that reacts with NaOH and is readily substituted by bromine. Dehydration with concentrated H₂SO₄ gives an ether near 140 °C and an alkene near 170 °C.

How to use

Keep one Reagent fixed and step through each Compound, pressing Run each time, so students can compare the four results side by side. Then keep the Compound fixed and change the Reagent. With CuO, heated or Concentrated H₂SO₄ (dehydration), move the Temperature slider to find the conditions each reaction needs. Ask students to predict every outcome, and the class of the alcohol, before they press Run.

Parameters you can change

  • Compound Ethanol (primary), Propan-2-ol (secondary), 2-Methylpropan-2-ol (tertiary), Phenol C₆H₅OH
  • Reagent Sodium metal, CuO, heated, Concentrated H₂SO₄ (dehydration), Bromine water, NaOH solution
  • Temperature 20–200 °C
  • Animation speed 0.5–3 ×

Questions to explore

  1. Why does 2-methylpropan-2-ol give no reaction with heated CuO, while propan-2-ol turns the black CuO red?
  2. Which reagents react with phenol but not with ethanol, and what does this show about phenol's acidity?
  3. At what temperature does concentrated H₂SO₄ turn ethanol into an alkene rather than an ether?