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

Leaving Group Conversions - Sulfonyl Chlorides

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions - Sulfonyl Chlorides

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2:16 minutes

Problem 24a

Textbook Question

Predict the product of the following sulfonylation reactions.
(a)

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Identify the functional groups present in the reactants. Sulfonylation typically involves a sulfonyl chloride (R-SO2-Cl) reacting with an alcohol or amine.

Determine the nucleophile in the reaction. In sulfonylation, the nucleophile is usually the oxygen atom in an alcohol or the nitrogen atom in an amine.

Consider the mechanism of the reaction. Sulfonylation involves the nucleophilic attack on the sulfur atom of the sulfonyl chloride, leading to the displacement of the chloride ion.

Predict the structure of the product. The nucleophile will form a bond with the sulfur atom, resulting in the formation of a sulfonate ester (if an alcohol is used) or a sulfonamide (if an amine is used).

Verify the stereochemistry and regiochemistry of the product, if applicable. Ensure that the product is correctly drawn with the appropriate orientation and connectivity.

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Key Concepts

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

Sulfonylation Reaction

Sulfonylation is a chemical reaction where a sulfonyl group is introduced into an organic molecule. This typically involves the reaction of an organic compound with a sulfonyl chloride in the presence of a base, resulting in the formation of a sulfonamide or sulfone. Understanding the mechanism and conditions of sulfonylation is crucial for predicting the products of such reactions.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In sulfonylation, recognizing the functional groups present in the reactants, such as amines or alcohols, is essential as they determine the site of reaction and the type of product formed, such as sulfonamides or sulfones.

Reaction Mechanism

The reaction mechanism describes the step-by-step process by which reactants are transformed into products. In sulfonylation, the mechanism often involves nucleophilic attack on the sulfonyl chloride by a nucleophile, followed by the formation of a stable product. Understanding the mechanism helps in predicting the structure and properties of the reaction product.

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Related Practice

Textbook Question

Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:

Textbook Question

Show how you would convert propan-1-ol to the following compounds using tosylate intermediates. You may use whatever additional reagents are needed.

a. 1-bromopropane

b. propan-1-amine, CH₃CH₂CH₂NH₂

Textbook Question

Predict the product for each of the following reactions.

(a)

Textbook Question

Predict the product for each of the following reactions.

(b)

Textbook Question

On the reaction coordinate diagram for the disfavored nucleophilic displacement of hydroxide, predict the curve that would demonstrate how using a tosylate makes the substitution favorable.

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Textbook Question

The sulfur atom in toluene sulfonyl chloride (TsCl) is strongly electrophilic. Why?

Textbook Question

Predict the product for each of the following reactions.

(d)

Textbook Question

A trifluoromethanesulfonate (triflate) can be used in a manner similar to tosylates. Which would you expect to be a better leaving group? Why?

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