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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3:54 minutes

Problem 92b

Textbook Question

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

Verified step by step guidance

Identify the starting alcohol: Analyze the target molecule to determine the appropriate alcohol that can be used as the starting material. The target molecule contains a thioether linkage, suggesting that the alcohol should be a primary alcohol with a similar carbon skeleton.

Convert the alcohol to a tosylate: React the identified alcohol with p-toluenesulfonyl chloride (TsCl) in the presence of a base like pyridine. This will convert the alcohol into a tosylate, which is a good leaving group.

Perform nucleophilic substitution: Use a thiol (R-SH) as the nucleophile to perform a nucleophilic substitution reaction on the tosylate. The thiol will replace the tosylate group, forming the thioether linkage present in the target molecule.

Ensure the correct carbon skeleton: Verify that the carbon skeleton of the starting alcohol matches the target molecule. If necessary, adjust the carbon chain length or branching before tosylation to ensure the final product has the correct structure.

Check stereochemistry and functional groups: Ensure that any stereochemistry or additional functional groups in the target molecule are correctly represented in the final product. Adjust the synthesis steps if needed to achieve the desired configuration.

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Key Concepts

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

Tosylate Formation

Tosylates are formed by reacting an alcohol with tosyl chloride (TsCl) in the presence of a base. This reaction converts the alcohol into a better leaving group, the tosylate, which can facilitate nucleophilic substitution reactions. Understanding this transformation is crucial for synthesizing target molecules from alcohols.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule with a nucleophile. There are two main mechanisms: SN1, which is unimolecular and involves carbocation formation, and SN2, which is bimolecular and involves a direct attack by the nucleophile. Recognizing which mechanism to apply is essential for predicting the outcome of the synthesis.

Stereochemistry in Organic Synthesis

Stereochemistry refers to the spatial arrangement of atoms in molecules and is critical in organic synthesis, especially when creating chiral centers. The configuration of the starting materials and the reaction conditions can lead to different stereoisomers. Understanding how to control stereochemistry is vital for synthesizing specific target molecules with desired properties.

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Related Practice

Textbook Question

Predict the products of the following reactions.

(a) cyclohexylmethanol + TsCl/pyridine

(b) product of (a) + LiAlH4

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

Predict the product of the following sulfonylation reactions.

(d)

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)

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

Key Concepts

Tosylate Formation

Nucleophilic Substitution Reactions

Stereochemistry in Organic Synthesis

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