Draw the complete mechanism for the Fischer esterification reaction performed. In this experiment, acetic acid (a carboxylic acid with the structure CH₃COOH) was reacted with 1-butanol (a primary alcohol with the structure CH₃(CH₂)₃OH) in the presence of concentrated sulfuric acid (H₂SO₄) as a catalyst. The goal of this reaction was to synthesize butyl acetate (an ester with the structure CH₃COO(CH₂)₃CH₃) as the final product, with water (H₂O) as the by-product.In the mechanism:Show how sulfuric acid protonates the carbonyl oxygen of acetic acid to activate it for nucleophilic attack.Illustrate the nucleophilic attack by 1-butanol on the protonated acetic acid.Include all intermediate structures, such as the tetrahedral intermediate formed after the nucleophilic attack.Show the steps leading to the formation of butyl acetate, including the removal of water as a leaving group and the regeneration of the sulfuric acid catalyst.Use curved arrows to indicate the flow of electrons at each step and label all key intermediates and transitions clearly.

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Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter15: An Introduction To Organometallic Compounds

Section15.1: Organomagnesium And Organolithium Compounds

Problem 15.2P: Recalling the reactions of alcohols from Chapter 10, show how to synthesize each compound from an...

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Draw the complete mechanism for the Fischer esterification reaction performed. In this experiment, acetic acid (a carboxylic acid with the structure CH₃COOH) was reacted with 1-butanol (a primary alcohol with the structure CH₃(CH₂)₃OH) in the presence of concentrated sulfuric acid (H₂SO₄) as a catalyst. The goal of this reaction was to synthesize butyl acetate (an ester with the structure CH₃COO(CH₂)₃CH₃) as the final product, with water (H₂O) as the by-product.

In the mechanism:

Show how sulfuric acid protonates the carbonyl oxygen of acetic acid to activate it for nucleophilic attack.
Illustrate the nucleophilic attack by 1-butanol on the protonated acetic acid.
Include all intermediate structures, such as the tetrahedral intermediate formed after the nucleophilic attack.
Show the steps leading to the formation of butyl acetate, including the removal of water as a leaving group and the regeneration of the sulfuric acid catalyst.
Use curved arrows to indicate the flow of electrons at each step and label all key intermediates and transitions clearly.

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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