Numford
Organic conversion

Ethanol to ethyl ethanoate

2 steps: oxidation, then esterification

Class 12, Chapter 7 Alcohols, Phenols and Ethers; Class 12, Chapter 8 Aldehydes, Ketones and Carboxylic Acids

  1. OH
    EthanolCH₃CH₂OHAlcohol
  2. Step 1

    KMnO₄, KOH, heat; then H₃O⁺

    i

    Alkaline KMnO₄ oxidises a primary alcohol all the way to the acid.

    Also written: K₂Cr₂O₇, H₂SO₄

    OOH
    Ethanoic acidCH₃COOHCarboxylic acid
  3. Step 2

    CH₃CH₂OH, conc. H₂SO₄ (catalyst), heat

    Esterification
    i

    Fischer esterification is reversible; remove water or use excess alcohol.

    OO
    Ethyl ethanoateCH₃COOCH₂CH₃Ester

Exam answer

  1. Step 1: Ethanol to ethanoic acid: KMnO₄, KOH, heat; then H₃O⁺.
  2. Step 2: Ethanoic acid to ethyl ethanoate: CH₃CH₂OH, conc. H₂SO₄ (catalyst), heat.
Alternative routes (4)
  • Ethanol → Ethanal → Ethanoic acid → Ethyl ethanoate
    1. Ethanol to ethanal: PCC.
    2. Ethanal to ethanoic acid: KMnO₄, dilute H₂SO₄.
    3. Ethanoic acid to ethyl ethanoate: CH₃CH₂OH, conc. H₂SO₄ (catalyst), heat.
  • Ethanol → Ethanoic acid → Ethanoyl chloride → Ethyl ethanoate
    1. Ethanol to ethanoic acid: KMnO₄, KOH, heat; then H₃O⁺.
    2. Ethanoic acid to ethanoyl chloride: SOCl₂.
    3. Ethanoyl chloride to ethyl ethanoate: CH₃CH₂OH, pyridine.
  • Ethanol → Ethanoic acid → Ethanoic anhydride → Ethyl ethanoate
    1. Ethanol to ethanoic acid: KMnO₄, KOH, heat; then H₃O⁺.
    2. Ethanoic acid to ethanoic anhydride: conc. H₂SO₄ (or P₂O₅), heat.
    3. Ethanoic anhydride to ethyl ethanoate: CH₃CH₂OH.
  • Ethanol → Ethanal → Ethanoic acid → Ethanoyl chloride → Ethyl ethanoate
    1. Ethanol to ethanal: PCC.
    2. Ethanal to ethanoic acid: KMnO₄, dilute H₂SO₄.
    3. Ethanoic acid to ethanoyl chloride: SOCl₂.
    4. Ethanoyl chloride to ethyl ethanoate: CH₃CH₂OH, pyridine.
Why these reagents

Reagent and reason, step by step

  • Step 1: Ethanol to ethanoic acid: KMnO₄, KOH, heat; then H₃O⁺ Alkaline KMnO₄ oxidises a primary alcohol all the way to the acid.
  • Step 2: Ethanoic acid to ethyl ethanoate: CH₃CH₂OH, conc. H₂SO₄ (catalyst), heat Fischer esterification is reversible; remove water or use excess alcohol.
Questions

Ethanol to ethyl ethanoate: quick answers

How many steps does it take to convert ethanol to ethyl ethanoate?

2 steps: Ethanol, then ethanoic acid, then ethyl ethanoate.

Which named reaction is used to convert ethanol to ethyl ethanoate?

Esterification. A carboxylic acid reacts with an alcohol in the presence of a few drops of concentrated H2SO4 to give an ester and water. Acid chlorides and anhydrides also give esters.

What is the reagent for step 1 of ethanol to ethyl ethanoate?

Ethanol to ethanoic acid: KMnO₄, KOH, heat; then H₃O⁺. Alkaline KMnO₄ oxidises a primary alcohol all the way to the acid.

Plan your own conversion