Hey guys, now we're going to talk about one of the more important mechanisms in this course and that is the mechanism of Fischer esterification. Fischer esterification is just another name for acid-catalyzed esterification. When you think about what that is, that would just mean that I'm taking a carboxylic acid. I'm reacting it with alcohol in the presence of acid and I'm getting an ester. I'm getting an ester product, hence the term esterification. According to our three rules, this is a totally fine reaction because we said that carboxylic acids and esters have about the same reactivity, so it's pretty easy to switch between the two. According to my three rules, I know this is a favorite reaction. I know that this can work. Why do I have this video? Because it turns out that professors just love to ask about this mechanism because it's kind of one of the fundamental mechanisms of nucleophilic acyl substitution. That's why I'm going to go into depth and we're going to draw the whole mechanism for this from scratch. So let's go ahead and do that now.
22. Carboxylic Acid Derivatives: NAS
Fischer Esterification
22. Carboxylic Acid Derivatives: NAS
Fischer Esterification - Video Tutorials & Practice Problems
Fischer Esterification is also known as acid-catalyzed esterification. Why is it so important? Because we convert an OH group to an OR group.
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concept
General Reaction
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Video transcript
![Content](https://cdn.clutchprep.com/guide_visuals/inline_images/dFrJXlI_vYguhyxwxQ7R2g.png)
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concept
General Mechanism
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Mechanism:
![Content](https://cdn.clutchprep.com/guide_visuals/inline_images/C3g6rZYiJmcWxH8cnhb41w.png)
BTW if you notice that when drawing the first resonance structure in red there is an arrow that looks off, don't be alarmed! The arrow should go the opposite direction [from the double bond to the +OH group]
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Additional resources for Fischer Esterification
PRACTICE PROBLEMS AND ACTIVITIES (15)
- Predict the esterification products of the following acid/alcohol pairs. (a) CH3CH2CH2COOH + CH3OH (b) CH3O...
- When butanoic acid and 18^O-labeled methanol react under acidic conditions, what compounds are labeled when th...
- a. A student did not obtain any ester when he added 2,4,6-trimethylbenzoic acid to an acidic solution of ethan...
- Propose a mechanism for the following reaction. (HINT: Number the carbons to help you see where they end up ...
- Show how each of the following esters could be prepared using a carboxylic acid as one of the starting materia...
- (b) Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
- Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for...
- Show how you would accomplish the following syntheses in good yields. (c) (d)
- Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for...
- Suggest the most appropriate reagent for each synthesis, and explain your choice.(b) <IMAGE>
- Show how you would convert alanine to the following derivatives. Show the structure of the product in each ca...
- Show how each of the following compounds can be prepared, using the given starting material: a. b.
- Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solve...
- Show the alcohol and the acid chloride that combine to make the following esters.(c) <IMAGE>(d) <IMAG...
- The mechanism of the Fischer esterification was controversial until 1938, when Irving Roberts and Harold Urey ...