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

Previous problemNext problem

Problem 24b

Textbook Question

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

Verified step by step guidance

Identify the reactants involved in the sulfonylation reaction. The first reactant is a sulfonyl chloride, specifically para-toluenesulfonyl chloride, and the second reactant is a cyclohexanol derivative.

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

Understand the mechanism of the reaction. The hydroxyl group (OH) on the cyclohexanol acts as a nucleophile and attacks the sulfur atom of the sulfonyl chloride, leading to the displacement of the chloride ion (Cl-).

Consider the stereochemistry of the reaction. Since the hydroxyl group is attached to a cyclohexane ring, the reaction may proceed with retention of configuration, depending on the reaction conditions.

Predict the product of the reaction. The product will be a sulfonate ester, where the cyclohexanol derivative is now bonded to the sulfonyl group, forming a cyclohexyl para-toluenesulfonate.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

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, as the sulfonyl group acts as an electrophile. Recognizing the conditions and directing effects of substituents on the aromatic ring is vital for predicting the outcome of the reaction.

Reaction Mechanism

A reaction mechanism describes the step-by-step process by which reactants are converted into products. In the context of sulfonylation, understanding the mechanism helps in predicting the structure of the final product, including the role of intermediates and the transition states. Familiarity with mechanisms allows chemists to anticipate the behavior of different substrates under varying conditions.

Watch next

Master Learning the mechanism of Sulfonyl Chlorides. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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.

<IMAGE>

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?

Textbook Question

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

(a)

Textbook Question

(a) Show how you would affect the following transformation using a tosylate.

(b) Why might this not be the most sustainable method?

Textbook Question

What is the product of each of the following reactions?

Textbook Question

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

a. CH₃CH₂CH₂SCH₂CH₃

Show more practices