Hydrolysis co product

Overview

Hydrolysis of an ester also regenerates the alcohol component.

Transformation

Esters → Alcohols

Equation

R-CO2R' + H2O <-> R-CO2H + R'OH

Reagents

dilute H2SO4(aq)

Environment

heat under reflux

Reaction class

hydrolysis

Mechanism

ester hydrolysis

Evidence level

textbook core

Scope and limitations

Scope

Acid-catalysed ester hydrolysis forms an alcohol together with the carboxylic acid product.

Limitations

This record is the alcohol coproduct branch of acid hydrolysis. Alkaline hydrolysis also forms the alcohol but gives a carboxylate salt rather than a carboxylic acid before work-up.

Related reactions

• Chlorination: Alcohols → Chloroalkanes

  Alcohols can be converted into chloroalkanes to create a better leaving group for downstream substitution.

• Chlorination with thionyl chloride: Alcohols → Chloroalkanes

  Thionyl chloride converts alcohols into chloroalkanes with sulfur dioxide and hydrogen chloride as by-products.

• Bromination: Alcohols → Bromoalkanes

  Bromide and acid conditions convert alcohols into bromoalkanes.

• Iodination: Alcohols → Iodoalkanes

  Iodine and red phosphorus conditions convert alcohols into iodoalkanes.

• Hydrolysis: Chloroalkanes → Alcohols

  The C-Cl bond can be displaced by hydroxide to form an alcohol.

• Hydrolysis: Bromoalkanes → Alcohols

  The C-Br bond can be displaced by hydroxide to form an alcohol.

• Hydrolysis: Iodoalkanes → Alcohols

  The C-I bond can be displaced by hydroxide to form an alcohol.

• Oxidation: Alcohols → Aldehydes

  Controlled oxidation of a primary alcohol gives an aldehyde.

• Oxidation: Alcohols → Ketones

  Oxidation of a secondary alcohol gives a ketone.

• Oxidation: Alcohols → Carboxylic acids

  Full oxidation of a primary alcohol gives a carboxylic acid.

• Hydration: Alkenes → Alcohols

  Catalytic hydration converts alkenes into alcohols.

• Dehydration: Alcohols → Alkenes

  Dehydration converts alcohols into alkenes.

• Esterification: Carboxylic acids → Esters

  Carboxylic acids react with alcohols to form esters.

• Esterification co reactant: Alcohols → Esters

  Alcohols combine with carboxylic acids to form esters.

• Hydrolysis: Esters → Carboxylic acids

  Hydrolysis converts esters back into carboxylic acid products.

• Acylation: Acyl chlorides → Esters

  Alcohol acylation converts acyl chlorides into esters.

References

1. Organic Chemistry: Chemistry of EstersJohn McMurry · OpenStax Organic Chemistry · 2023

   Distinguishes reversible acid-catalysed ester hydrolysis from alkaline saponification, which gives a carboxylate ion until a separate acidification step.