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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5:19 minutes

Problem 4a

Textbook Question

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

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Identify the functional groups in the reactant and determine the type of reaction taking place (e.g., substitution, addition, elimination, etc.). Specific-acid catalysis typically involves protonation of a functional group to make it more reactive.

Protonate the most likely site on the reactant using a proton (H⁺) from the acid catalyst. This step increases the electrophilicity of the molecule, making it more susceptible to nucleophilic attack or other transformations.

Determine the next step in the mechanism based on the protonated intermediate. For example, if a carbocation is formed, consider whether a nucleophile will attack or if a rearrangement might occur.

Draw the intermediate structures for each step of the reaction, ensuring that all charges and lone pairs are accounted for. Use curved arrows to show the movement of electrons during bond formation and bond breaking.

Conclude the mechanism by showing the final product and regenerating the acid catalyst (if applicable). Verify that the overall reaction is consistent with the principles of specific-acid catalysis.

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Key Concepts

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

Specific Acid Catalysis

Specific acid catalysis refers to the acceleration of a chemical reaction by the addition of an acid that donates protons (H+) to the reactants. In this process, the acid interacts with the substrate, enhancing its electrophilicity and facilitating the formation of a transition state. This mechanism is crucial in organic reactions, particularly in hydration and esterification, where protonation of functional groups can significantly lower the activation energy.

Reaction Mechanism

A reaction mechanism is a detailed step-by-step description of the pathway through which reactants are converted into products. It outlines the sequence of elementary steps, including bond breaking and formation, and the role of catalysts. Understanding the mechanism is essential for predicting the outcome of reactions and for designing new synthetic pathways in organic chemistry.

Proton Transfer

Proton transfer is a fundamental process in acid-base chemistry where a proton (H+) is transferred from an acid to a base. In the context of specific acid catalysis, this transfer is often the first step, leading to the activation of the substrate. This concept is vital for understanding how acids can enhance reaction rates and alter the stability of intermediates in organic reactions.

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Related Practice

Textbook Question

c. What is the electrophile in the first step?

d. What is the nucleophile in the first step?

Textbook Question

e. What is the electrophile in the second step?

f. What is the nucleophile in the second step?

Textbook Question

Ethers can be synthesized by substituting ethanol for water in the acid-catalyzed hydration reaction. Suggest an arrow-pushing mechanism which accounts for the formation of the ethyl ether under these conditions.

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 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

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

Textbook Question