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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4:30 minutes

Problem 45b

Textbook Question

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.
(b) n-butyl phenyl ether from phenol and butan-1-ol

Verified step by step guidance

Step 1: Begin by recognizing that phenol (C₆H₅OH) is an aromatic alcohol and butan-1-ol (CH₃CH₂CH₂CH₂OH) is a primary alcohol. To synthesize n-butyl phenyl ether, you need to form an ether bond (C-O-C) between the phenol and butan-1-ol.

Step 2: Convert phenol into its phenoxide ion (C₆H₅O⁻) by treating it with a strong base such as sodium hydroxide (NaOH). This deprotonates the hydroxyl group of phenol, making it more nucleophilic.

Step 3: Prepare butan-1-ol for the reaction by converting it into a good electrophile. This can be achieved by reacting butan-1-ol with a strong acid like sulfuric acid (H₂SO₄) or phosphorus tribromide (PBr₃) to form butyl bromide (CH₃CH₂CH₂CH₂Br), a primary alkyl halide.

Step 4: Perform the Williamson ether synthesis, which involves reacting the phenoxide ion (C₆H₅O⁻) with butyl bromide (CH₃CH₂CH₂CH₂Br). The phenoxide ion acts as a nucleophile and attacks the electrophilic carbon in the butyl bromide, displacing the bromide ion (Br⁻) and forming n-butyl phenyl ether (C₆H₅OCH₂CH₂CH₂CH₃).

Step 5: Purify the product by distillation or recrystallization, depending on the physical properties of n-butyl phenyl ether, to ensure a good yield of the desired ether.

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Key Concepts

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

Ethers and Their Synthesis

Ethers are organic compounds characterized by an oxygen atom connected to two alkyl or aryl groups. The synthesis of ethers can be achieved through various methods, including the Williamson ether synthesis, which involves the nucleophilic substitution of an alkoxide ion with a primary alkyl halide. Understanding the reactivity and properties of ethers is crucial for designing effective synthetic routes.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions are fundamental in organic chemistry, where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the context of synthesizing n-butyl phenyl ether, the nucleophile is the alkoxide ion derived from butan-1-ol, which reacts with phenol. The mechanism can follow either an SN1 or SN2 pathway, depending on the structure of the reactants.

Reactivity of Alcohols and Phenols

Alcohols and phenols exhibit different reactivities due to their structural features. Alcohols can be converted into alkoxide ions, which are strong nucleophiles, while phenols can act as electrophiles in nucleophilic substitution reactions. The acidity of phenols allows for the formation of phenoxide ions, enhancing their reactivity in ether synthesis, particularly when reacting with alkyl halides.

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Textbook Question

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.

(a) cyclopentyl n-propyl ether from cyclopentanol and propan-1-ol

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.)

(d) 1-methoxy-1-methylcyclopentane

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.)

f. tert-butyl phenyl ether

Textbook Question

(e) 1-isopropoxy-1-methylcyclopentane

Textbook Question

Both LiAlH₄ and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that become protonated in an aqueous workup). Those alkoxides can react with 1° or methyl alkyl halides or tosylates to give ethers. Show how the following ethers can be formed in this two-step process. As starting materials you may use any reactants containing 7 carbons or fewer.

(b)

Textbook Question

(c)

Textbook Question

In Chapter 14, we saw that Agent Orange contains (2,4,5-trichlorophenoxy) acetic acid, called 2,4,5-T. This compound is synthesized by the partial reaction of 1,2,4,5-tetrachlorobenzene with sodium hydroxide, followed by reaction with sodium chloroacetate, ClCH₂CO₂Na.

a. Draw the structures of these compounds, and write equations for these reactions.

Textbook Question

Design a synthesis for each of the following, using an intramolecular reaction:

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