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 drawn
Structure of methyl ethanoate
Esters Examples Table
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
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
- 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
- The acid anhydrides are more reactive than carboxylic acids
- The reaction is not reversible and a higher yield is achieved.