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 - Alkoxymercuration

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Making Ethers - Alkoxymercuration

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2:57 minutes

Problem 48b

Textbook Question

In light of your answer to Assessment 9.47, predict the product of the following reactions we have seen previously where an alcohol is substituted for water.
(b)

Verified step by step guidance

Identify the type of reaction: Since the problem involves substituting alcohol for water, consider the mechanism of nucleophilic substitution or elimination reactions where alcohol acts as a nucleophile or solvent.

Determine the role of alcohol: Alcohol can act as a nucleophile due to the presence of the hydroxyl group (-OH), which can participate in reactions similar to water, but with different reactivity due to its organic nature.

Consider the reaction conditions: Assess whether the reaction conditions favor substitution or elimination. Factors such as temperature, solvent, and presence of acids or bases can influence the pathway.

Predict the product formation: Based on the mechanism, predict the possible products. If alcohol acts as a nucleophile, it may replace a leaving group in the substrate, forming an ether. Alternatively, if elimination is favored, an alkene may form.

Review stereochemistry and regiochemistry: Consider any stereochemical or regiochemical outcomes based on the structure of the starting materials and the mechanism of the reaction. This will help in predicting the major product.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of alcohols, the hydroxyl group can act as a nucleophile, attacking electrophilic centers to form new bonds, often resulting in the substitution of water or other leaving groups.

Alcohol Reactivity

Alcohols are versatile compounds in organic reactions due to their ability to act as both nucleophiles and electrophiles. Their reactivity is influenced by the presence of the hydroxyl group, which can be protonated to form a better leaving group, facilitating substitution reactions. Understanding the conditions that enhance alcohol reactivity is crucial for predicting reaction outcomes.

Reaction Mechanism

A reaction mechanism outlines the step-by-step process by which reactants transform into products. It includes the identification of intermediates, transition states, and the role of catalysts or solvents. For predicting products in alcohol substitution reactions, understanding the mechanism helps in visualizing how the alcohol interacts with other reactants and the sequence of bond-breaking and bond-forming events.

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