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 - Alcohol Condensation

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Alcohol Condensation

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7:05 minutes

Problem 77b

Textbook Question

Propose a mechanism for each of the following reactions:
b.

Verified step by step guidance

Step 1: Analyze the reactant structure. The molecule contains two hydroxyl (-OH) groups attached to a bicyclic system. The reaction conditions include concentrated sulfuric acid (H₂SO₄) and heat (Δ), which suggests an acid-catalyzed dehydration reaction leading to the formation of a ketone.

Step 2: Protonation of one of the hydroxyl groups. In the presence of H₂SO₄, one of the hydroxyl groups is protonated, forming a good leaving group (water). This step increases the electrophilicity of the carbon attached to the hydroxyl group.

Step 3: Loss of water to form a carbocation. The protonated hydroxyl group leaves as water, generating a carbocation intermediate. The stability of the carbocation is enhanced by the bicyclic structure, which can undergo rearrangement if necessary.

Step 4: Intramolecular rearrangement and formation of a ketone. The carbocation undergoes a hydride shift or alkyl shift to stabilize the intermediate, followed by the migration of a bond to form a double bond (C=O) at the appropriate position, resulting in the ketone product.

Step 5: Final product formation. The reaction concludes with the formation of the bicyclic ketone structure as shown in the product. The sulfuric acid acts as a catalyst and is regenerated at the end of the reaction.

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Key Concepts

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

Esterification Reaction

Esterification is a chemical reaction that forms an ester from an alcohol and a carboxylic acid, often in the presence of an acid catalyst. In this case, the reaction involves alcohols converting to ethers, which is a related process. The acid catalyst, such as sulfuric acid (H2SO4), helps to protonate the alcohol, making it a better leaving group and facilitating the formation of the ether.

Protonation and Leaving Groups

Protonation is the addition of a proton (H+) to a molecule, which can enhance its reactivity. In the context of this reaction, the hydroxyl group (-OH) of the alcohol is protonated by H2SO4, converting it into a better leaving group (water). This step is crucial for the subsequent nucleophilic attack that leads to ether formation.

Nucleophilic Substitution Mechanism

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In this reaction, the ether formation involves the nucleophilic attack of the alcohol on the electrophilic carbon of the protonated alcohol, leading to the formation of the ether product. Understanding this mechanism is essential for proposing the correct reaction pathway.

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Related Practice

Textbook Question

1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol.

(a) Show what alcohol will undergo condensation, with loss of water, to give 1,4-dioxane.

(b) Propose a mechanism for this reaction.

Textbook Question

Contrast the mechanisms of the two preceding reactions, the dehydration and condensation of ethanol.

Textbook Question

Explain why bimolecular condensation is a poor method for making unsymmetrical ethers such as ethyl methyl ether.

Textbook Question

Propose a mechanism for the acid-catalyzed condensation of n-propyl alcohol to n-propyl ether, as shown above. When the temperature is allowed to rise too high, propene is formed. Propose a mechanism for the formation of propene, and explain why it is favored at higher temperatures.

Textbook Question

Heating an alcohol with sulfuric acid is a good way to prepare a symmetrical ether such as diethyl ether.

b. How would you synthesize ethyl propyl ether?

Textbook Question

Propose a mechanism for each of the following reactions:

Textbook Question

Heating an alcohol with sulfuric acid is a good way to prepare a symmetrical ether such as diethyl ether.

a. Explain why it is not a good way to prepare an unsymmetrical ether such as ethyl propyl ether.

Textbook Question

Which of the following ethers would be obtained in greatest yield directly from alcohols?

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