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Saponification quiz

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  • What is saponification in organic chemistry?
    Saponification is the base-catalyzed hydrolysis of an ester, resulting in the formation of a carboxylate anion and an alcohol.
  • What are the reactants required for saponification?
    The reactants are an ester, water, and a base catalyst.
  • What is the main product of saponification when no protonation step is included?
    The main product is a carboxylate anion (carboxylate salt) instead of a carboxylic acid.
  • Why does saponification yield a carboxylate anion instead of a carboxylic acid?
    Because the base present deprotonates the carboxylic acid, leaving a carboxylate anion.
  • What type of reaction mechanism is saponification?
    Saponification follows a nucleophilic acyl substitution (NAS) mechanism.
  • What is the first step in the saponification mechanism?
    The first step is a nucleophilic attack by the base on the ester’s carbonyl carbon.
  • What intermediate is formed during saponification?
    A tetrahedral intermediate is formed after the nucleophilic attack.
  • Which group is expelled as the leaving group during saponification?
    The OR group (alkoxy group) is expelled as the leaving group.
  • What are the final products of saponification?
    The final products are a carboxylate anion and an alcohol.
  • How does the base-catalyzed mechanism of ester hydrolysis compare to the acid-catalyzed mechanism?
    The base-catalyzed mechanism is generally simpler and does not require protonation or resonance activation of the carbonyl.
  • What role does the base play in the saponification reaction?
    The base acts as a nucleophile and also deprotonates the carboxylic acid formed, yielding a carboxylate anion.
  • Why is protonation not required in the base-catalyzed mechanism?
    Because the nucleophile is already negatively charged and strong enough to attack the carbonyl carbon directly.
  • What happens if you protonate the carboxylate product after saponification?
    If you protonate the carboxylate, you obtain a carboxylic acid.
  • What is the significance of the tetrahedral intermediate in saponification?
    The tetrahedral intermediate is a key step where the nucleophile has added to the carbonyl carbon before the leaving group is expelled.
  • What is the other product formed alongside the carboxylate anion in saponification?
    An alcohol is formed as the other product.