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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4:20 minutes

Problem 13

Textbook Question

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

Verified step by step guidance

Analyze the target compound: The given compound is a tertiary alcohol with the structure 2,3-dimethyl-2-butanol. This indicates that the preparation involves the addition of a hydroxyl group (-OH) to a carbon atom in a highly substituted environment.

Select an appropriate alkene: To prepare this compound, the starting alkene should be 2,3-dimethyl-2-butene, as it has the same carbon skeleton as the target compound and can undergo hydration to form the alcohol.

Choose the reaction conditions: The hydration of the alkene can be achieved using acid-catalyzed hydration (e.g., H₂SO₄ and water) or oxymercuration-demercuration (using Hg(OAc)₂ and NaBH₄). These methods ensure Markovnikov addition, where the hydroxyl group attaches to the more substituted carbon.

Explain the mechanism: In acid-catalyzed hydration, the alkene undergoes protonation to form a carbocation intermediate at the more substituted carbon. Water then attacks the carbocation, followed by deprotonation to yield the alcohol. In oxymercuration-demercuration, the alkene reacts with Hg(OAc)₂ to form a mercurinium ion intermediate, which is then attacked by water. Reduction with NaBH₄ replaces the mercury group with a hydrogen atom, forming the alcohol.

Verify the product: Ensure that the reaction conditions lead to the formation of 2,3-dimethyl-2-butanol as the major product, with the hydroxyl group attached to the tertiary carbon. This matches the structure of the target compound.

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Key Concepts

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

Alkene Reactivity

Alkenes are unsaturated hydrocarbons characterized by at least one carbon-carbon double bond. Their reactivity is primarily due to this double bond, which can undergo various reactions such as electrophilic addition, polymerization, and alkoxylation. Understanding how alkenes react is crucial for synthesizing compounds, as they can serve as versatile starting materials in organic reactions.

Alkoxylation

Alkoxylation is a chemical reaction where an alkene reacts with an alcohol in the presence of an acid catalyst to form an ether. This process involves the formation of a carbocation intermediate, which can then react with the alcohol to yield the ether product. Recognizing the mechanism of alkoxylation is essential for preparing ethers from alkenes, as it highlights the importance of regioselectivity and stereochemistry in the reaction.

Ether Synthesis

Ethers are organic compounds characterized by an oxygen atom bonded to two alkyl or aryl groups. They can be synthesized through various methods, including the alkoxylation of alkenes, as well as through the dehydration of alcohols. Understanding the structural features and reactivity of ethers is important for predicting their behavior in chemical reactions and their applications in organic synthesis.

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