haya.Learning made clear
Reactions due to α-hydrogen, the Cannizzaro reaction and ring substitution sheet
5-mark answer frame

What is aldol condensation? Explain it with the equation for ethanal. How does it differ from the Cannizzaro reaction? Write the Cannizzaro reaction of methanal.

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

  1. 1 · Define. Aldehydes or ketones with at least one α-hydrogen, in dilute alkali, join to give a β-hydroxy aldehyde (aldol) or ketone (ketol), which loses water on heating.
  2. 2 · Explain the α-hydrogen. It is acidic: C=O pulls electrons, and the enolate ion is resonance-stabilised. OH⁻ removes it; the enolate attacks the C=O of a second molecule.
  3. 3 · Write the ethanal equations. 2CH₃CHO ⇌ (dil. NaOH) CH₃CH(OH)CH₂CHO → (heat) CH₃CH=CHCHO + H₂O.
  4. 4 · Draw and label. Draw 3-hydroxybutanal and mark the α and β carbons; then draw but-2-enal with the C=C between them.
  5. 5 · Write the Cannizzaro reaction. No α-H, concentrated alkali: 2HCHO + KOH → CH₃OH + HCOOK. One molecule is reduced, one oxidised (disproportionation).
  6. 6 · Contrast the two. Aldol: α-H, dilute alkali, new C-C bond. Cannizzaro: no α-H, concentrated alkali, oxidation-reduction.
  7. 7 · Close in one line. So the presence or absence of an α-hydrogen decides which reaction a carbonyl compound gives.

Scoring tip: Always state 'dilute' for aldol and 'concentrated' for Cannizzaro, and name both products of the Cannizzaro reaction.