Carboxylic Acids - What Is Fischer Esterification?

5 important questions on Carboxylic Acids - What Is Fischer Esterification?

What is Fischer esterification?

Fischer esterification is the formation of an ester by treatment of a carboxylic acid with an alcohol in the presence of an acid catalyst.

How can you predict the product of a Fischer esterification?

In a Fischer esterification to -OH group of the carboxyl is replaced with an -OR group.

What are the six common mechanistic patterns for organic reactions?

1. Addition of a proton
2. Removal of a proton
3. Reaction between an electrophile and a nucleophile
4. Rearrangement of a bond
5. Breaking of a bond to form a stable ion or molecule
6. Collapse of a tetrahedral carbonyl addition intermediate to eject a leaving group and regenerate the carbonyl group.
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In a Fischer esterification H2SO4 is used as an acid catalyst, how will the sulfuric acid react with the alcohol?

The sulfuric acid is a stronger acid than the conjugated acid of an alcohol and will donate a proton to the alcohol.

What are the steps in the Fischer esterification mechanism?

1. Addition of a proton to the carbonyl group.
2. Reaction between an electrophile (protonated carboxyl group) and a nucleophile (alcohol) to form an oxonium ion.
3. Removal of a proton from oxonium ion to an alcohol resulting in a tetrahedral carbonyl addition intermediate.
4. Addition of a proton to the hydroxyl group forming a good leaving group.
5. Collapse of the tetrahedral carbonyl addition intermediate, ejecting the leaving group and regenerating the carbonyl group.

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