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 26a

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)

Verified step by step guidance

Step 1: Begin with the alkene, cyclopentene. The first step is to perform a hydroboration-oxidation reaction to convert the alkene into an alcohol. Use BH3 followed by H2O2 and NaOH to achieve this transformation, resulting in cyclopentanol.

Step 2: Convert the alcohol into a tosylate. Treat cyclopentanol with p-toluenesulfonyl chloride (TsCl) in the presence of a base like pyridine. This will form cyclopentyl tosylate, which is a good leaving group.

Step 3: Perform a nucleophilic substitution reaction to replace the tosylate group with a cyano group. Use sodium cyanide (NaCN) as the nucleophile. The tosylate group will leave, and the cyano group will attach, forming cyclopentyl cyanide.

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Key Concepts

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

Tosylate Formation

Tosylate formation involves converting an alcohol into a tosylate ester using tosyl chloride (TsCl) in the presence of a base. This reaction enhances the leaving group ability of the alcohol, making it more reactive in subsequent nucleophilic substitution reactions. The tosylate group is a good leaving group, facilitating the formation of various products in organic synthesis.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions are fundamental processes in organic chemistry where a nucleophile replaces a leaving group in a molecule. These reactions can occur via two main mechanisms: SN1, which involves a two-step process with a carbocation intermediate, and SN2, which is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. Understanding these mechanisms is crucial for predicting the outcomes of syntheses.

Multistep Synthesis

Multistep synthesis refers to the process of constructing complex organic molecules through a series of sequential reactions. Each step typically involves the transformation of reactants into intermediates and finally into the desired product. Mastery of multistep synthesis is essential for chemists, as it allows for the strategic planning of synthetic routes to achieve specific molecular architectures efficiently.