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Ester Hydrolysis Calculator

Breaking down an ester with water or alkali.

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Carboxylate Salt

Formula first

Overview

Base-promoted ester hydrolysis, often referred to as saponification, is a nucleophilic substitution reaction where a hydroxide ion attacks the carbonyl carbon of an ester. This reaction proceeds irreversibly to produce a carboxylate salt and an alcohol, unlike acid-catalyzed hydrolysis which remains in equilibrium.

Symbols

Variables

RCOOR' = Ester, NaOH = Sodium Hydroxide, RCOONa = Carboxylate Salt, R'OH = Alcohol

RCOOR'
Ester
mol
NaOH
Sodium Hydroxide
mol
RCOONa
Carboxylate Salt
mol
R'OH
Alcohol
mol

Apply it well

When To Use

When to use: Apply this equation when calculating reactant requirements or product yields for the breakdown of esters in strongly basic solutions. It assumes a 1:1 molar stoichiometry between the ester and the sodium hydroxide for complete conversion into salt and alcohol.

Why it matters: This reaction is the chemical foundation for the industrial manufacture of soap from fats and oils. It is also a vital tool in analytical chemistry for determining the saponification value of unknown lipid samples and in organic synthesis for deprotecting carboxylic acids.

Avoid these traps

Common Mistakes

  • Confusing acid and base products.
  • Thinking both are reversible.
  • Wrong products for saponification.

One free problem

Practice Problem

A chemist hydrolyzes 2.50 moles of ethyl acetate using an excess of sodium hydroxide. Calculate the total number of moles of sodium acetate (salt) formed at the end of the reaction.

Ester2.5 mol
Sodium Hydroxide5 mol

Solve for: salt

Hint: In this balanced chemical equation, the molar ratio between the ester and the resulting carboxylate salt is 1:1.

The full worked solution stays in the interactive walkthrough.

References

Sources

  1. Clayden, Greeves, Warren. Organic Chemistry.
  2. Bruice, Paula Yurkanis. Organic Chemistry.
  3. Wikipedia: Ester hydrolysis
  4. IUPAC Gold Book
  5. IUPAC Gold Book: Stoichiometric coefficient
  6. Atkins' Physical Chemistry (any recent edition)
  7. Wikipedia: Stoichiometry
  8. Clayden, J., Greeves, N., & Warren, S. (2012). Organic Chemistry (2nd ed.). Oxford University Press.