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 27

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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Verified step by step guidance

Begin by understanding the reaction coordinate diagram, which plots the energy changes during a chemical reaction. The x-axis represents the progress of the reaction, while the y-axis represents the energy level.

Identify the initial state of the reactants and the final state of the products on the diagram. For a disfavored nucleophilic displacement of hydroxide, the energy of the transition state is typically high, making the reaction less favorable.

Introduce the concept of a tosylate group. Tosylates are excellent leaving groups due to their ability to stabilize the negative charge, thus lowering the energy of the transition state.

Predict how the curve would change with the use of a tosylate. The energy barrier (activation energy) should decrease, making the transition state lower in energy compared to the original reaction with hydroxide.

Visualize the new curve on the diagram. The curve should show a lower peak for the transition state, indicating a more favorable reaction pathway with the tosylate as the leaving group.

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Key Concepts

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

Reaction Coordinate Diagram

A reaction coordinate diagram is a graphical representation of the energy changes that occur during a chemical reaction. It plots the potential energy of the system as the reaction progresses from reactants to products. Key features include the energy of activation, transition states, and the overall energy change, which help in understanding the reaction's kinetics and thermodynamics.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental type of reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. The reaction can proceed via two main mechanisms: SN1, which involves a two-step process with a carbocation intermediate, and SN2, which is a one-step bimolecular process. The nature of the nucleophile, leaving group, and substrate significantly influences the reaction pathway and rate.

Tosylate as a Leaving Group

Tosylate (p-toluenesulfonate) is a superior leaving group compared to hydroxide due to its ability to stabilize the negative charge through resonance and its large size, which disperses charge. In nucleophilic substitution reactions, replacing a poor leaving group like hydroxide with tosylate can make the reaction more favorable by lowering the activation energy, thus enhancing the reaction rate and yield.

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