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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4:28 minutes

Problem 17b

Textbook Question

(b) Finish the solution for Solved Problem 20-1 by providing a mechanism for the acid-catalyzed hydrolysis of ethyl formate.

Verified step by step guidance

Identify the reaction type: The problem involves the acid-catalyzed hydrolysis of ethyl formate, which is an ester. This reaction will produce a carboxylic acid (formic acid) and an alcohol (ethanol). The mechanism proceeds through nucleophilic acyl substitution under acidic conditions.

Step 1: Protonation of the ester carbonyl group. The acid catalyst (H⁺) protonates the carbonyl oxygen of ethyl formate, increasing the electrophilicity of the carbonyl carbon. This makes it more susceptible to nucleophilic attack.

Step 2: Nucleophilic attack by water. A water molecule acts as a nucleophile and attacks the carbonyl carbon, forming a tetrahedral intermediate. This intermediate contains a positively charged oxygen atom due to the protonated carbonyl group.

Step 3: Proton transfer. A proton transfer occurs within the intermediate to stabilize the structure. The hydroxyl group (from water) becomes neutral, and one of the ethoxy groups is protonated, making it a good leaving group.

Step 4: Elimination of the leaving group and deprotonation. The ethoxy group (C₂H₅O⁺) leaves, forming ethanol. The remaining intermediate is protonated formic acid, which undergoes deprotonation to yield the final product: formic acid (HCOOH).

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Key Concepts

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

Acid-Catalyzed Hydrolysis

Acid-catalyzed hydrolysis is a reaction where water is used to break down a compound in the presence of an acid, which increases the reaction rate. In this process, the acid donates protons (H+) to the reactants, facilitating the cleavage of bonds and the formation of products. This mechanism is crucial for understanding how esters, like ethyl formate, are converted into their corresponding acids and alcohols.

Mechanism of Ester Hydrolysis

The mechanism of ester hydrolysis involves several key steps: protonation of the carbonyl oxygen, nucleophilic attack by water, and subsequent deprotonation. Initially, the acid protonates the carbonyl oxygen, increasing the electrophilicity of the carbon atom. Water then acts as a nucleophile, attacking the carbonyl carbon, leading to the formation of a tetrahedral intermediate, which eventually collapses to yield the acid and alcohol.

Role of Ethyl Formate

Ethyl formate is an ester formed from formic acid and ethanol. In the context of acid-catalyzed hydrolysis, it serves as the substrate that undergoes reaction with water in the presence of an acid catalyst. Understanding the structure and reactivity of ethyl formate is essential for predicting the products of the hydrolysis reaction, which will yield formic acid and ethanol.

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