WAEC 2023 Chemistry · Question 13

Which of the following reactions represents the hydrolysis of an alkanoate?

Options

  1. A.CH3COOH+OH−⇌H+⇌CH3COO−+H2OCH_3COOH + OH^- ⇌H^+⇌ CH_3COO^- + H_2O
  2. B.CH3COOH+C2H5OH⇌H+⇌CH3COOC2H5+H2OCH_3COOH + C_2H_5OH ⇌H^+⇌ CH_3COOC_2H_5 + H_2O
  3. C.CH3COOC2H5+H2O⇌H+⇌CH3COO−+CH3CH2OHCH_3COOC_2H_5 + H_2O ⇌H^+⇌ CH_3COO^- + CH_3CH_2OH
  4. D.CH3COOCH2CH3+H2O⇌H+⇌CH3COOH+CH3CH2OHCH_3COOCH_2CH_3 + H_2O ⇌H^+⇌ CH_3COOH + CH_3CH_2OH

Answer: D. CH3COOCH2CH3+H2O⇌H+⇌CH3COOH+CH3CH2OHCH_3COOCH_2CH_3 + H_2O ⇌H^+⇌ CH_3COOH + CH_3CH_2OH

Explanation written with AI and checked against the answer key

Analyze the question: Hydrolysis of an alkanoate (an ester) means the ester reacts with water to break down into its parent carboxylic acid and alcohol. With an acid catalyst (H⁺), the reaction is reversible.

Concept: RCOOR' + H₂O ⇌ (H⁺) RCOOH + R'OH

This is the reverse of esterification (Fischer esterification).

Check each option:

  • A. CH₃COOH + OH⁻ → CH₃COO⁻ + H₂O is a neutralisation (acid-base) reaction, not hydrolysis.
  • B. CH₃COOH + C₂H₅OH → CH₃COOC₂H₅ + H₂O is esterification, the formation of an ester. This is the reverse of hydrolysis.
  • C. CH₃COOC₂H₅ + H₂O → CH₃COO⁻ + CH₃CH₂OH starts with an ester and water, but the product is the carboxylate ion. That is characteristic of alkaline hydrolysis (saponification, with OH⁻), not the acid-catalysed pathway shown with H⁺. It is also not balanced for charge, since the H⁺ is not accounted for. So it is not the best representation.
  • D. CH₃COOCH₂CH₃ + H₂O ⇌ (H⁺) CH₃COOH + CH₃CH₂OH takes ethyl ethanoate plus water and gives ethanoic acid and ethanol. This is a correct, balanced acid-catalysed hydrolysis of an ester.

Tip: Remember "ester + water → acid + alcohol" for hydrolysis, and "acid + alcohol → ester + water" for esterification. If the ester is hydrolysed with a base (NaOH), you get the carboxylate salt and alcohol instead, and this is called saponification.

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