Esters (OCR A Level Chemistry)

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Esterification of Carboxylic Acids & Acid Anhydrides

  • Esters are a carboxylic acid derivative which contains the ester group, -COO-
  • An ester is named after the parent carboxylic acid from which it is derived
  • The nomenclature of esters follows the pattern:
    • Remove the -oic acid suffix from the parent carboxylic acid and replace with -oate
    • The alkyl chain attached to the oxygen atom of the -COO- group is then added as the first word in the name
      • This part of the name comes from the alcohol, e.g. propanol becomes propyl

  • Ester names are confusing because the name is written backwards from the way the structure is drawn7.3.2 Structure of methyl ethanoate, downloadable AS & A Level Chemistry revision notes

Structure of methyl ethanoate

Esters Examples Table

Esters example table, downloadable AS & A Level Chemistry revision notes

Esterification

  • Esters are characterised by their sweet and fruity smells
  • They are prepared from the condensation reaction between a carboxylic acid and alcohol with concentrated H2SO4 as catalyst
    • This is also called esterification

  • A condensation reaction involves the elimination of a small molecule not always water
    • Esterification is one example of a condensation reaction as water is eliminated from the acid and alcohol reacting together
  • The reaction is reversible
  • The reaction is quite slow and needs heating under reflux, (often for several hours or days).
  • Low yields(50% ish) tend to be achieved by this route

Carboxylic Acids & Derivatives Production of Esters, downloadable AS & A Level Chemistry revision notes

Esters are formed from the condensation reaction between carboxylic acids and alcohols

  • Esterification can also take place by reacting acid anhydrides with alcohols at room temperature

6-3-2-acid-anhydride-ester-formation

 

  • Acid anhydrides are also derivatives of carboxylic acids formed by substitution of the -OH group by an alkanoate (e.g. ethanoate, propanoate)
    • Acid anhydrides are named by identifying the parent hydrocarbon chain and adding the suffix -oic anhydride
    • They can also be named by removing the -oic acid from the carboxylic acid and adding -oic anyhydride

6-3-2-general-acid-anhydride-structure

 

  • The acid anhydrides are more reactive than carboxylic acids
  • The reaction is not reversible and a higher yield is achieved.

Hydrolysis of Esters

  • Esters can be hydrolysed to reform the carboxylic acid and alcohol by either dilute acid or dilute alkali and heat
  • When an ester is heated under reflux with dilute acid (eg. sulfuric acid) an equilibrium mixture is established as the reaction is reversible

Ester hydrolysis by dilute acid is a reversible reaction forming carboxylic acid and alcohol

  • However, heating the ester under reflux with dilute alkali (eg. sodium hydroxide) is an irreversible reaction as the ester is fully hydrolysed
  • This results in the formation of a sodium carboxylate salt which needs further acidification to turn into a carboxylic acid
    • The sodium carboxylate (-COO-) ion needs to get protonated by an acid (such as HCl) to form the carboxylic acid (-COOH)

Ester hydrolysis by dilute alkali is an irreversible reaction forming a sodium carboxylate salt and alcohol

Table showing differences in hydrolysis of esters

Table for hydrolysis of esters, downloadable AS & A Level Chemistry revision notes

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Sonny

Author: Sonny

Expertise: Chemistry

Sonny graduated from Imperial College London with a first-class degree in Biomedical Engineering. Turning from engineering to education, he has now been a science tutor working in the UK for several years. Sonny enjoys sharing his passion for science and producing engaging educational materials that help students reach their goals.