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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1:25 minutes

Problem 59c,d

Textbook Question

What products would you expect to obtain from the following reactions?
c. urea + water
d. β-ethylglutaric acid + acetyl chloride + Δ

Verified step by step guidance

Step 1: Analyze the reaction between urea and water. Urea is a compound with the formula (NH2)2CO, containing two amine groups and a carbonyl group. Water (H2O) can act as a reactant in hydrolysis reactions.

Step 2: Recognize that hydrolysis of urea typically involves breaking the C-N bonds adjacent to the carbonyl group. This reaction is catalyzed by enzymes like urease in biological systems, but under chemical conditions, it can proceed with heat or acid/base catalysis.

Step 3: Predict the products of hydrolysis. The carbonyl group reacts with water, leading to the formation of carbon dioxide (CO2) and ammonia (NH3). This is a decomposition reaction.

Step 4: Write the balanced chemical equation for the reaction. The hydrolysis of urea can be represented as:

{({NH 2}^{2})}_{CO} + {H 2}_{O} \to CO 2 + NH 3

Step 5: For part d, analyze the reaction between beta-ethylglutaric acid, acetyl chloride, and heat (Δ). This reaction likely involves acylation or condensation. Beta-ethylglutaric acid has two carboxylic acid groups and a beta-ethyl substituent. Acetyl chloride is a reactive acylating agent. Heat promotes the formation of an anhydride or ester. Predict the product based on the functional groups involved and write the mechanism for the reaction.

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Key Concepts

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

Hydrolysis of Urea

Hydrolysis of urea involves the reaction of urea with water, typically catalyzed by an acid or base. This reaction leads to the formation of ammonia and carbon dioxide. Understanding this process is crucial for predicting the products of the reaction, as it illustrates how urea can break down in the presence of water.

Acid-Catalyzed Reactions

Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In the context of ester hydrolysis, the acid donates protons, facilitating the breakdown of esters into their corresponding alcohols and acids. Recognizing the role of acid in these reactions is essential for understanding the mechanisms and products formed.

Acyl Chlorides and Their Reactivity

Acyl chlorides are highly reactive compounds that can undergo various reactions, including acylation and hydrolysis. When reacted with carboxylic acids or alcohols, they typically yield esters. Understanding the reactivity of acyl chlorides is important for predicting the products of the reaction involving beta-ethylglutaric acid and acetyl chloride.

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Related Practice

Textbook Question

Propose mechanisms for the following reactions.

(c)

Textbook Question

Propose mechanisms for the following reactions.

(d)

Textbook Question

The mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, except that the nitrile is first protonated, activating it toward attack by a weak nucleophile (water). Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzed hydrolysis of benzonitrile to benzamide.

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.

4. acid-catalyzed hydrolysis of an amide

Textbook Question

Which ester hydrolyzes more rapidly? a. methyl acetate or phenyl acetate?

Textbook Question

Which ester hydrolyzes more rapidly? b. phenyl acetate or benzyl acetate?

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

Textbook Question

For each heterocyclic compound,

(ii) show what compounds would result from complete hydrolysis.

(a)

(b)

(c)

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