Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

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3:47 minutes

Problem 49a,b

Textbook Question

Propose mechanisms for the following reactions.
(a)
(b)

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Step 1 (Reaction a): Identify the reactants and the product. The reactants are an acyl chloride (CH3COCl) and an alcohol (CH3CH2OH). The product is an ester (CH3COOCH2CH3). This reaction is an esterification reaction involving nucleophilic acyl substitution.

Step 2 (Reaction a): The mechanism begins with the nucleophilic attack of the alcohol's oxygen atom on the carbonyl carbon of the acyl chloride. This forms a tetrahedral intermediate.

Step 3 (Reaction a): The tetrahedral intermediate collapses, expelling the chloride ion (Cl⁻) as a leaving group and forming the ester bond (CH3COOCH2CH3).

Step 4 (Reaction b): Identify the reactants and the products. The reactant is an ester (CH3COOCH3), and the products are a carboxylic acid (CH3COOH) and methanol (CH3OH). This reaction is a base-catalyzed hydrolysis of an ester, also known as saponification.

Step 5 (Reaction b): The mechanism begins with the hydroxide ion (OH⁻) attacking the carbonyl carbon of the ester, forming a tetrahedral intermediate. The intermediate then collapses, expelling the methoxide ion (CH3O⁻) as a leaving group. The methoxide ion reacts with water to form methanol (CH3OH), while the remaining structure forms the carboxylic acid (CH3COOH).

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Ester Hydrolysis

Ester hydrolysis is a chemical reaction where an ester reacts with water to form an alcohol and a carboxylic acid. This reaction can occur under acidic or basic conditions, with the mechanism differing based on the environment. In acid-catalyzed hydrolysis, the ester is protonated, making it more susceptible to nucleophilic attack by water, while in base-catalyzed hydrolysis, hydroxide ions act as the nucleophile.

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of a leaving group. This mechanism is crucial in understanding reactions involving esters and acid chlorides, as it explains how nucleophiles can replace the leaving group, resulting in the formation of new products.

Mechanism of Acid-Catalyzed Reactions

In acid-catalyzed reactions, the presence of an acid enhances the electrophilicity of the carbonyl carbon, facilitating nucleophilic attack. The mechanism typically involves protonation of the carbonyl oxygen, followed by nucleophilic attack by water or alcohol, and subsequent deprotonation to yield the final products. Understanding this mechanism is essential for predicting the outcomes of reactions involving esters and acid chlorides.

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The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in an equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH₂CH₃.

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Propose mechanisms for the following reactions. (a) (b)

Key Concepts

Ester Hydrolysis

Nucleophilic Acyl Substitution

Mechanism of Acid-Catalyzed Reactions

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Propose mechanisms for the following reactions.
(a)
(b)