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

Nucleophilic Acyl Substitution

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

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2:53 minutes

Problem 51d

Textbook Question

What compounds are obtained from the following hydrolysis reactions?
d.

Verified step by step guidance

Identify the functional group in the compound: The given compound contains two ester groups. Esters undergo hydrolysis in the presence of water, typically catalyzed by an acid or base.

Understand the reaction mechanism: During hydrolysis, the ester bond is cleaved, resulting in the formation of a carboxylic acid and an alcohol. Each ester group will produce one carboxylic acid and one alcohol.

Analyze the structure: The first ester group (connected to the cyclopentane ring) will yield cyclopentane carboxylic acid (C5H9COOH) and ethanol (CH3CH2OH) upon hydrolysis.

Analyze the second ester group: The second ester group (connected to the ethyl group) will yield propanoic acid (CH3CH2COOH) and ethanol (CH3CH2OH) upon hydrolysis.

Combine the products: The hydrolysis of the given compound will result in two carboxylic acids (cyclopentane carboxylic acid and propanoic acid) and two alcohol molecules (ethanol).

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Key Concepts

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

Hydrolysis of Carboxylic Acid Derivatives

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the context of carboxylic acid derivatives, such as esters or anhydrides, hydrolysis typically results in the formation of a carboxylic acid and an alcohol or another relevant product. Understanding this reaction is crucial for predicting the products formed when these compounds react with water.

Functional Groups in Organic Chemistry

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the given reaction, the presence of carbonyl groups (C=O) indicates that the compound is likely a carboxylic acid derivative. Recognizing these functional groups helps in predicting the behavior of organic compounds during chemical reactions.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of how a chemical reaction occurs at the molecular level. For hydrolysis reactions, understanding the mechanism can help explain how water interacts with the substrate, leading to the cleavage of bonds and formation of products. This knowledge is essential for predicting the outcome of the reaction and understanding the stability of intermediates formed during the process.