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

Williamson Ether Synthesis

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Williamson Ether Synthesis

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Problem 17

Textbook Question

Predict the product when the dihydroxybenzene shown is treated with a single equivalent of both base and haloalkane.

Verified step by step guidance

Identify the functional groups in the dihydroxybenzene. The compound has two hydroxyl (OH) groups and a nitro (NO2) group attached to a benzene ring.

Recognize that the reaction involves a base (NaOH) and a haloalkane. The base will deprotonate one of the hydroxyl groups, forming a phenoxide ion.

Determine which hydroxyl group is more acidic. The presence of the electron-withdrawing nitro group increases the acidity of the hydroxyl group ortho to it, making it more likely to be deprotonated.

Consider the nucleophilic substitution reaction. The phenoxide ion, being a strong nucleophile, will attack the haloalkane, displacing the bromide ion and forming an ether linkage.

Predict the product structure. The reaction will result in the formation of an ether, where the alkyl group from the haloalkane is attached to the oxygen of the deprotonated hydroxyl group on the benzene ring.

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Key Concepts

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

Dihydroxybenzene Reactivity

Dihydroxybenzenes, also known as catechols or resorcinols, contain two hydroxyl (-OH) groups on a benzene ring. The position of these groups affects the reactivity of the compound, particularly in nucleophilic substitution reactions. Understanding how these substituents influence electron density and steric hindrance is crucial for predicting the outcome of reactions with haloalkanes.

Nucleophilic Substitution Mechanism

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of haloalkanes, the reaction can proceed via either an SN1 or SN2 pathway, depending on the structure of the haloalkane and the conditions. Recognizing which mechanism is favored helps in predicting the product formed when a dihydroxybenzene reacts with a haloalkane.

Base-Driven Deprotonation

When a dihydroxybenzene is treated with a base, one of the hydroxyl groups can be deprotonated, generating a phenoxide ion. This ion is a stronger nucleophile than the neutral dihydroxybenzene, enhancing its reactivity towards electrophiles like haloalkanes. Understanding the role of the base in facilitating this deprotonation is essential for predicting the product of the reaction.

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Textbook Question

Show how the following ethers might be synthesized using (1) alkoxymercuration– demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)

a. 2-methoxybutane

b. ethyl cyclohexyl ether

c. 1-methoxy-2-methylcyclopentane

Textbook Question

There are two different ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. When pure (–)-octan-2-ol of specific rotation -8.24° is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoctane with a specific rotation of -15.6°. When pure (–)-octan-2-ol is treated with tosyl chloride and pyridine and then with sodium ethoxide, the product is also 2-ethoxyoctane. Predict the rotation of the 2-ethoxyoctane made using the tosylation/sodium ethoxide procedure, and propose a detailed mechanism to support your prediction.

Textbook Question

Propose a Williamson synthesis of 3-butoxy-1,1-dimethylcyclohexane from 3,3-dimethyl-cyclohexanol and butan-1-ol.

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Fluoxetine hydrochloride (Prozac®) is a widely used antidepressant. How might you stereoselectively install the indicated ether functional group (ROR) in (R)-fluoxetine?

Textbook Question

What is the product of the following reaction?

Textbook Question

Predict the product of the following substitution/addition reactions involving phenoxides.

(a)

Textbook Question

Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the other?].

(a)

Textbook Question

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

(a)

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