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

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Acid-Catalyzed Alkoxylation

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Acid-Catalyzed Alkoxylation

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12:56 minutes

Problem 72

Textbook Question

Draw a reaction coordinate diagram for the acid-catalyzed addition of an alcohol to an alkene. Which step is rate-determining?

Verified step by step guidance

Start by understanding the mechanism of the acid-catalyzed addition of an alcohol to an alkene. This reaction typically involves the formation of a carbocation intermediate.

Identify the key steps in the mechanism: protonation of the alkene to form a carbocation, nucleophilic attack by the alcohol, and deprotonation to form the final ether product.

Draw the reaction coordinate diagram. The x-axis represents the reaction progress, while the y-axis represents the energy. Begin with the reactants at a certain energy level.

Illustrate the energy changes for each step: the initial protonation step usually has a high energy barrier, forming the carbocation intermediate, which is often the highest energy point in the diagram.

Determine the rate-determining step. This is typically the step with the highest energy barrier, which is often the formation of the carbocation intermediate in this type of reaction.

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Key Concepts

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

Reaction Coordinate Diagram

A reaction coordinate diagram visually represents the energy changes during a chemical reaction. It plots the energy of the system against the progress of the reaction, illustrating the transition states and intermediates. The peaks correspond to transition states, while valleys represent stable intermediates. This diagram helps in understanding the energy barriers and the overall thermodynamics of the reaction.

Acid-Catalyzed Reaction Mechanism

In acid-catalyzed reactions, an acid donates a proton (H+) to facilitate the reaction, often enhancing the electrophilicity of the alkene. This mechanism typically involves the formation of a carbocation intermediate, which is more reactive towards nucleophiles, such as alcohols. Understanding this mechanism is crucial for predicting the reaction pathway and the stability of intermediates formed during the process.

Rate-Determining Step

The rate-determining step (RDS) is the slowest step in a reaction mechanism that dictates the overall reaction rate. It often involves the highest energy transition state and is crucial for understanding the kinetics of the reaction. Identifying the RDS allows chemists to focus on the most significant barriers to reaction progress, which is essential for optimizing reaction conditions and yields.

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Related Practice

Textbook Question

Show how you would accomplish the following transformations. Some of these examples require more than one step.

(a) 2-methylpropene → 2,2-dimethyloxirane

(b) 1-phenylethanol → 2-phenyloxirane

Textbook Question

Draw the mechanism for the following reaction if it involves specific-acid catalysis.

Textbook Question

Draw the mechanism if it involves general-acid catalysis.

Textbook Question

Identify the alkene and alcohol partners that could be used to make the following ethers.

(c)

Textbook Question

What is the major product of each of the following reactions?

Textbook Question

How could the following compounds be prepared using an alkene as one of the starting materials?

Textbook Question

Show how each of the following compounds can be synthesized from an alkene:

Textbook Question

a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

8. CH₃OH + H₂SO₄

b. With which reagents do the two alkenes react to form different products?

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