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

Transesterification

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Transesterification

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5:20 minutes

Problem 58a,b

Textbook Question

What reagents would you use to convert methyl propanoate to the following compounds?
a. isopropyl propanoate
b. sodium propanoate

Verified step by step guidance

Step 1: To convert methyl propanoate to isopropyl propanoate, perform a transesterification reaction. Use isopropanol (isopropyl alcohol) as the alcohol reagent and an acid catalyst such as sulfuric acid (H₂SO₄) to facilitate the exchange of the methyl group with the isopropyl group.

Step 2: Heat the reaction mixture to promote the transesterification process, ensuring the methyl group is replaced by the isopropyl group to form isopropyl propanoate.

Step 3: To convert methyl propanoate to sodium propanoate, perform a saponification reaction. Use a strong base such as sodium hydroxide (NaOH) to hydrolyze the ester bond in methyl propanoate.

Step 4: During saponification, the ester bond is broken, yielding propanoic acid and methanol. The propanoic acid reacts with the sodium hydroxide to form sodium propanoate.

Step 5: Isolate the sodium propanoate by neutralizing the reaction mixture and removing any excess water or byproducts.

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Key Concepts

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

Transesterification

Transesterification is a chemical reaction where an ester reacts with an alcohol to form a different ester and a new alcohol. This process involves the exchange of the alkoxy group of the ester with the alcohol, which is crucial for converting methyl propanoate to isopropyl propanoate. The reaction typically requires an acid or base catalyst to proceed efficiently.

Saponification

Saponification is the process of converting an ester into a carboxylic acid and an alcohol through hydrolysis, usually in the presence of a strong base like sodium hydroxide. In the context of the question, it is relevant for converting methyl propanoate to sodium propanoate, where the ester is hydrolyzed to yield the sodium salt of the corresponding acid.

Reagents for Ester Reactions

The choice of reagents is critical in ester reactions. For transesterification, an alcohol (like isopropanol) is needed, while for saponification, a strong base (such as sodium hydroxide or sodium carbonate) is required. Understanding the role of these reagents helps in determining the correct pathway for the desired product transformations.

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Related Practice

Textbook Question

Predict the products of the following reactions.

(g)

Textbook Question

Acid-catalyzed transesterification:

Complete the mechanism for this acid-catalyzed transesterification by drawing out all the individual steps. Draw the important resonance contributors for each resonance-stabilized intermediate.

Textbook Question

Starting with methyl acetate, what neutral nucleophile would you use to synthesize each of the following compounds? a. ethyl acetate

Textbook Question

1,4-Diazabicyclo[2.2.2]octane (abbreviated DABCO) is a tertiary amine that catalyzes transesterification reactions. Explain how it does this.

Textbook Question

What products are obtained from the following reactions? b. phenyl acetate + excess ethanol + HCl

Textbook Question

Write the mechanism for the acid-catalyzed transesterification of ethyl acetate with methanol.

Textbook Question

Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.

(a) n-octyl formate

(b) n-octyl acetate

Textbook Question

Propose a mechanism for the following ring-opening transesterification. Use the mechanism in Problem 21-13 as a model.

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