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 22

Textbook Question

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

Verified step by step guidance

Examine the structure of toluene sulfonyl chloride (TsCl). The sulfur atom is bonded to two oxygen atoms, one chlorine atom, and a benzene ring through a sulfonyl group.

Recognize that the sulfur atom in TsCl is part of a sulfonyl group, which is characterized by the presence of two double-bonded oxygen atoms. These oxygen atoms are highly electronegative.

Understand that the electronegative oxygen atoms withdraw electron density from the sulfur atom through resonance and inductive effects, making the sulfur atom electron-deficient.

Consider the role of the chlorine atom, which is also electronegative and can further withdraw electron density from the sulfur atom through inductive effects, enhancing the electrophilicity of the sulfur.

Conclude that the combination of electron-withdrawing effects from the oxygen and chlorine atoms makes the sulfur atom in TsCl a strong electrophile, as it seeks to accept electrons to alleviate its electron deficiency.

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Key Concepts

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

Electrophilicity

Electrophilicity refers to the tendency of a species to accept electrons. Electrophiles are typically positively charged or neutral species with an incomplete octet, making them reactive towards nucleophiles. In the case of toluene sulfonyl chloride, the sulfur atom is electrophilic due to its ability to attract electron pairs from nucleophiles, facilitating chemical reactions.

Sulfonyl Chloride Structure

Sulfonyl chlorides, like toluene sulfonyl chloride, contain a sulfonyl group (SO2) bonded to a chlorine atom. The sulfur atom in this group is bonded to two oxygen atoms via double bonds and to a chlorine atom, creating a highly polarized structure. This polarization enhances the electrophilic character of sulfur, making it more susceptible to nucleophilic attack.

Resonance Stabilization

Resonance stabilization occurs when a molecule can be represented by multiple valid Lewis structures, leading to a delocalization of electrons. In toluene sulfonyl chloride, the resonance between the sulfur and oxygen atoms allows for the distribution of positive charge, increasing the electrophilicity of the sulfur atom. This delocalization makes the sulfur more reactive towards nucleophiles.

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Related Practice

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

Predict the product of the following sulfonylation reactions.

(a)

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

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 of the following sulfonylation reactions.

(b)

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)

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