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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2:47 minutes

Problem 68d

Textbook Question

What are the products of the following reactions?
d.

Verified step by step guidance

Step 1: Identify the functional group in the reactant. The given compound is phthalic anhydride, which contains an anhydride functional group. Anhydrides are reactive towards water and undergo hydrolysis.

Step 2: Understand the reaction mechanism. When anhydrides react with water, they are hydrolyzed to form two carboxylic acids. The reaction involves the cleavage of the anhydride bond.

Step 3: Predict the products. Hydrolysis of phthalic anhydride will yield phthalic acid, which has two carboxylic acid groups attached to a benzene ring.

Step 4: Write the chemical equation for the reaction. The reaction can be represented as:

Phthalic Anhydride + H 2 O \to Phthalic Acid

Step 5: Note the structural change. The anhydride ring opens up, and two hydroxyl groups from water are added to form two carboxylic acid groups. This is a typical hydrolysis reaction for anhydrides.

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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, but in this case, it is acid-catalyzed, which means an acid is used to speed up the reaction. The presence of the acid helps to protonate the carbonyl oxygen, making the carbon more electrophilic and facilitating the nucleophilic attack by water.

Acid-Catalyzed Reaction Mechanism

In acid-catalyzed reactions, the acid donates a proton (H+) to a reactant, enhancing its reactivity. For ester hydrolysis, the acid protonates the carbonyl oxygen of the ester, increasing the electrophilicity of the carbonyl carbon. This step is crucial as it allows water, acting as a nucleophile, to attack the carbonyl carbon, leading to the cleavage of the ester bond and the formation of the products.

Products of Hydrolysis

The products of ester hydrolysis are typically a carboxylic acid and an alcohol. In the case of the given reaction, the ester structure shown will yield a specific carboxylic acid and an alcohol upon hydrolysis. Identifying the structure of the starting ester is essential to predict the exact products formed after the reaction with water.

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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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What are the products of the following reactions? d.

Key Concepts

Ester Hydrolysis

Acid-Catalyzed Reaction Mechanism

Products of Hydrolysis

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What are the products of the following reactions?
d.