Alright, so we learned about the Fischer esterification from carboxylic acids and alcohols and their hydrolysis in acidic or basic conditions but what is transesterification?
Transesterification is the conversion of one ester to another – simple:
Just like the Fischer esterification and ester hydrolysis, it is also a reversible reaction. Therefore, if we use a large excess of the alcohol, it is going to act as a nucleophile and, in a series of reversible steps, eventually replace the alkoxide in the ester:
Transesterification can also be achieved by using the conjugate base of an alcohol and in this case, the mechanism if similar to the base-catalyzed hydrolysis of esters:
As usual, the reacting alkoxide should be used in excess in order to move the equilibrium to the right.
Transesterification has many applications in biological systems and also for synthesizing polyethylene terephthalate (PET) which is a common polyester in the production of clothing, plastics, furniture, tires and many other products.
Need some good practice on the reactions of carboxylic acids and their derivatives?
Check this 45-question, Multiple-Choice Quiz with a 50-min Video Solution covering the reactions of acids, esters, lactones, amides, acid chlorides and etc.
Carboxylic Acids and Their Derivatives Quiz
Check Also
- Preparation of Carboxylic Acids
- Naming Carboxylic Acids
- Naming Nitriles
- Naming Esters
- Naming Carboxylic Acid Derivatives – Practice Problems
- Fischer Esterification
- Ester Hydrolysis by Acid and Base-Catalyzed Hydrolysis
- Esters Reaction with Amines – The Aminolysis Mechanism
- Ester Reactions Summary and Practice Problems
- Preparation of Acyl (Acid) Chlorides (ROCl)
- Reactions of Acid Chlorides (ROCl) with Nucleophiles
- R2CuLi Organocuprates – Gilman Reagent
- Reaction of Acyl Chlorides with Grignard and Gilman (Organocuprate) Reagents
- Reduction of Acyl Chlorides by LiAlH4, NaBH4, and LiAl(OtBu)3H
- Preparation and Reaction Mechanism of Carboxylic Anhydrides
- Amides – Structure and Reactivity
- Naming Amides
- Amides Hydrolysis: Acid and Base-Catalyzed Mechanism
- Amide Dehydration Mechanism by SOCl2, POCl3, and P2O5
- Amide Reduction Mechanism by LiAlH4
- Reduction of Amides to Amines and Aldehydes
- Amides Preparation and Reactions Summary
- Amides from Carboxylic Acids-DCC and EDC Coupling
- The Mechanism of Nitrile Hydrolysis To Carboxylic Acid
- Nitrile Reduction Mechanism with LiAlH4 and DIBAL to Amine or Aldehyde
- The Mechanism of Grignard and Organolithium Reactions with Nitriles
- The Reactions of Nitriles
- Converting Nitriles to Amides
- Carboxylic Acids to Ketones
- Esters to Ketones
- Carboxylic Acids and Their Derivatives Practice Problems
- Carboxylic Acids and Their Derivatives Quiz
- Reactions Map of Carboxylic Acid Derivatives