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 26c

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)

Verified step by step guidance

Identify the starting material as an alcohol, specifically 2-methyl-1-butanol.

Convert the alcohol to a tosylate. This involves treating the alcohol with tosyl chloride (TsCl) in the presence of a base like pyridine. The hydroxyl group is replaced by a tosylate group, forming 2-methyl-1-butyl tosylate.

Perform a nucleophilic substitution reaction. Use a thiol nucleophile, such as thiophenol (PhSH), to displace the tosylate group. This results in the formation of the desired thioether product, 2-methyl-1-butyl phenyl sulfide.

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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. Tosylates are excellent intermediates in organic synthesis, allowing for the formation of various functional groups.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions are fundamental processes in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. 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 characterized by a concerted mechanism. Understanding these mechanisms is crucial for predicting the outcomes of synthetic pathways.

Multistep Synthesis

Multistep synthesis refers to the process of constructing complex organic molecules through a series of sequential reactions. Each step typically involves the formation or transformation of specific functional groups, and the choice of reagents and conditions is critical for the success of the overall synthesis. Mastery of multistep synthesis is essential for chemists to design efficient pathways to target compounds.

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Related Practice

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

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

(b)

Textbook Question

Predict the product of the following sulfonylation reactions.

(d)

Textbook Question

Predict the product of the following sulfonylation reactions.

(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)

Textbook Question

Write the appropriate reagent over each arrow.

Textbook Question

Starting with (R)-1-deuterio-1-propanol, how could you prepare

a. (S)-1-deuterio-1-propanol?

Multiple Choice

Which of the following syntheses would be best to make the given molecule?

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