Chemistry College

The Fischer esterification mechanism is examined in this question. The overall reaction is: Benzoic acid, C H 3 O H and H C l react to form a methyl ester, H 2 O and H C l. Benzoic acid is a carboxylic acid bonded to a benzene ring. Identify the results or mechanism of each step.

Answers

Answer 1

Answer:

See explanation and image attached

Explanation:

Fischer esterification is a type of reaction used  to convert carboxylic acids to ester in the presence of excess alcohol and a strong acid which acts as a catalyst. Another final product formed in the reaction is water.

The mechanism for the fischer esterification of Benzoic acid and  C H 3 O H in the presence of HCl as the catalyst is shown in the image attached to this answer.

The final products of the reaction are methyl benzoate, water and H^+ as shown in the image attached.

Answer 2

The methyl ester, water, and the acid catalyst (HCl) are byproducts of the Fischer esterification process, which involves protonation, nucleophilic attack, elimination, and deprotonation processes.

Carbonyl oxygen protonation: The carbonyl oxygen of the carboxylic acid (benzoic acid) is protonated by the acid catalyst (HCl) in the first step. The protonation of the carbonyl carbon increases its electrophilicity and promotes the alcohol's nucleophilic assault. Attack by the alcohol's nucleophilic oxygen (methanol, CH3OH) on the protonated carboxylic acid's carbonyl carbon results in the formation of a tetrahedral intermediate. The acid catalyst also helps with this phase. Elimination of water: In the following step, the water molecule must be removed from the tetrahedral intermediate. The hydroxyl group (-OH) from the carboxylic acid and a hydrogen from the hydroxyl group of the alcohol are removed to create this water molecule. Deprotonation: A deprotonation occurs after the removal of water.

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