Difference between revisions of "Fischer esterification"
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| − | '''Fisher esterification''' is an organic chemical reaction in which an [[alcohol]] reacts with a [[carboxylic acid]] in the presence of a strong acid to create an [[ester]] and water. This is a coupling reaction. | + | '''Fisher esterification''' is an organic chemical reaction in which an [[alcohol]] reacts with a [[carboxylic acid]] in the presence of a strong acid to create an [[ester]] and water. This is a coupling reaction. It was first described by the chemists Hermann Emil Fischer and Arthur Speier. This is a dynamic reaction which exists in equilibrium. The chemists object is to manipulate concentration and conditions to drive the reaction towards the desired product before they die of old age. Fisher esterification is slow. It helps not a bit that in reverse, water hydrolyzes an ester to return the alcohol and the carboxylic acid. Both processes coexist, so the task is not easy. |
| − | == | + | ==Tactics== |
* Remove one of the products as the reaction proceeds to force the equilibrium in that direction. | * Remove one of the products as the reaction proceeds to force the equilibrium in that direction. | ||
* Start with as little water as possible. | * Start with as little water as possible. | ||
| Line 7: | Line 7: | ||
* Wear comfortable shoes. | * Wear comfortable shoes. | ||
| − | == | + | ==Examples== |
| − | + | A classic example is to distill glacial [[acetic acid]], anhydrous [[ethanol]] with concentrated [[sulfuric acid]] to give [[ethyl acetate]]. The resulting distillate can be then be further purified and re-distilled as described by [[https://www.erowid.org/archive/rhodium/chemistry/ethyl.acetate.html Erowid]]. | |
| − | A classic example is to distill glacial [[ | + | |
| − | + | ||
| − | + | ||
| + | ==Mechanism== | ||
Read about the mechanism [[http://chemwiki.ucdavis.edu/Core/Organic_Chemistry/Carboxylic_Acids/Reactivity_of_Carboxylic_Acids/Fischer_esterification here]] | Read about the mechanism [[http://chemwiki.ucdavis.edu/Core/Organic_Chemistry/Carboxylic_Acids/Reactivity_of_Carboxylic_Acids/Fischer_esterification here]] | ||
| − | == | + | ==Projects== |
| − | + | ||
* [[Methyl salicylate]] (Oil of Wintergreen) | * [[Methyl salicylate]] (Oil of Wintergreen) | ||
| − | * [[Dimethyl | + | * [[Dimethyl oxalate]] |
==References== | ==References== | ||
| + | <references/> | ||
| + | ===Relevant Sciencemadness threads=== | ||
[[Category:Reactions]] | [[Category:Reactions]] | ||
Revision as of 15:37, 27 March 2016
Fisher esterification is an organic chemical reaction in which an alcohol reacts with a carboxylic acid in the presence of a strong acid to create an ester and water. This is a coupling reaction. It was first described by the chemists Hermann Emil Fischer and Arthur Speier. This is a dynamic reaction which exists in equilibrium. The chemists object is to manipulate concentration and conditions to drive the reaction towards the desired product before they die of old age. Fisher esterification is slow. It helps not a bit that in reverse, water hydrolyzes an ester to return the alcohol and the carboxylic acid. Both processes coexist, so the task is not easy.
Contents
Tactics
- Remove one of the products as the reaction proceeds to force the equilibrium in that direction.
- Start with as little water as possible.
- Start with an excess of the alcohol and let Le Chatelier do the driving.
- Wear comfortable shoes.
Examples
A classic example is to distill glacial acetic acid, anhydrous ethanol with concentrated sulfuric acid to give ethyl acetate. The resulting distillate can be then be further purified and re-distilled as described by [Erowid].
Mechanism
Read about the mechanism [here]
Projects
- Methyl salicylate (Oil of Wintergreen)
- Dimethyl oxalate
