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

Previous problemNext problem

8:57 minutes

Problem 2(1)

Textbook Question

Compare each of the mechanisms listed here with the mechanism for each of the two parts of the acid-catalyzed hydrolysis of an ester, indicating a. similarities. b. differences.
1. acid-catalyzed formation of a hydrate

Verified step by step guidance

Step 1: Understand the acid-catalyzed hydrolysis of an ester. This reaction involves two main parts: (1) protonation of the ester carbonyl group to make it more electrophilic, followed by nucleophilic attack by water, and (2) subsequent steps leading to the formation of a carboxylic acid and an alcohol. Write the general mechanism for this reaction using curved arrows to show electron movement.

Step 2: Review the mechanism for the acid-catalyzed formation of a hydrate (Section 16.9). This reaction involves the protonation of a carbonyl group (e.g., in an aldehyde or ketone), followed by nucleophilic attack by water, and subsequent deprotonation to form a geminal diol (hydrate). Write the general mechanism for this reaction as well.

Step 3: Compare the similarities between the two mechanisms. For example, both mechanisms involve the protonation of a carbonyl group to increase its electrophilicity, nucleophilic attack by water, and subsequent proton transfer steps. Highlight these shared features in the context of the two reactions.

Step 4: Identify the differences between the two mechanisms. For instance, in the acid-catalyzed hydrolysis of an ester, the leaving group (alcohol) departs after nucleophilic attack, whereas in the formation of a hydrate, no leaving group is expelled. Additionally, the final products differ: a carboxylic acid and alcohol in ester hydrolysis versus a geminal diol in hydrate formation.

Step 5: Summarize the key points of comparison, emphasizing how the underlying principles of acid catalysis and nucleophilic attack are applied in both mechanisms, but the specific steps and outcomes differ due to the nature of the starting materials and intermediates.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Acid-Catalyzed Hydrolysis of Esters

Acid-catalyzed hydrolysis of esters involves the reaction of an ester with water in the presence of an acid catalyst, typically resulting in the formation of a carboxylic acid and an alcohol. The mechanism includes protonation of the carbonyl oxygen, nucleophilic attack by water, and subsequent deprotonation. Understanding this mechanism is crucial for comparing it with other acid-catalyzed reactions.

Mechanism of Hydrate Formation

The acid-catalyzed formation of a hydrate involves the addition of water to a carbonyl compound, such as an aldehyde or ketone, facilitated by an acid. The mechanism includes protonation of the carbonyl oxygen, followed by nucleophilic attack by water, leading to the formation of a geminal diol (hydrate). Recognizing this process helps in identifying similarities and differences with ester hydrolysis.

Comparison of Reaction Mechanisms

Comparing reaction mechanisms involves analyzing the steps and intermediates of different chemical reactions to identify common features and distinct pathways. This includes examining the role of catalysts, the nature of nucleophiles, and the stability of intermediates. Such comparisons enhance understanding of reaction dynamics and can reveal insights into reaction conditions and outcomes.

Watch next

Master General Reaction with a bite sized video explanation from Johnny

Start learning