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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Problem 24d

Textbook Question

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

Verified step by step guidance

Identify the functional groups in the starting material. The starting material is a cyclohexanol derivative with an alcohol group (OH) attached to the cyclohexane ring.

Recognize the reagent used in the reaction. The reagent is trifluoromethanesulfonyl chloride (CF3SO2Cl), which is similar to tosyl chloride (TsCl) and is used to convert alcohols into sulfonate esters.

Understand the role of the base, triethylamine (Et3N), in the reaction. The base is used to neutralize the hydrochloric acid (HCl) byproduct formed during the reaction, facilitating the formation of the sulfonate ester.

Predict the mechanism of the reaction. The alcohol oxygen will attack the sulfur atom of the trifluoromethanesulfonyl chloride, displacing the chloride ion and forming a trifluoromethanesulfonate ester.

Consider the stereochemistry of the product. Since the reaction involves the formation of a new bond at the oxygen atom, the stereochemistry at the carbon center attached to the oxygen remains unchanged. The product will be a trifluoromethanesulfonate ester with the same stereochemistry as the starting alcohol.

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Key Concepts

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

Sulfonylation

Sulfonylation is a chemical reaction that introduces a sulfonyl group (SO2) into a molecule. This process typically involves the reaction of a sulfonyl chloride with an organic compound, often an aromatic ring or an alcohol, leading to the formation of sulfonate esters or sulfonamides. Understanding the mechanism of this reaction is crucial for predicting the products formed.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This reaction is essential for understanding how sulfonyl groups can be introduced into aromatic compounds. The stability of the aromatic system and the nature of the substituents influence the regioselectivity of the reaction.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of sulfonylation, the position where the sulfonyl group attaches to the aromatic ring can vary based on existing substituents and their electronic effects. Recognizing these patterns is vital for accurately predicting the products of the reaction.

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Related Practice

Textbook Question

Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.

(a)

Textbook Question

Predict the major product(s) of each of the following reactions.

Textbook Question

Complete the following multistep syntheses using tosylate formation as one of the steps. The optimum number of steps for each synthesis is shown.

(a)

Textbook Question

Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.

(b)

Textbook Question

Predict the product of the following sulfonylation reactions.

(c)

Textbook Question

Complete the following multistep syntheses using tosylate formation as one of the steps. The optimum number of steps for each synthesis is shown.

(c)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃, and (iv) 1. TsCl, Et₃N 2. NaCN. If no reaction occurs, write 'no reaction.'

(k)

Textbook Question

Write the appropriate reagent over each arrow.

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