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 93

Textbook Question

(a) Show how you would affect the following transformation using a tosylate.
(b) Why might this not be the most sustainable method?
(c) What reagent might you use instead?

Verified step by step guidance

Step 1: Identify the functional group transformation. The problem involves converting an alcohol group (-OH) to a bromide group (-Br).

Step 2: Use a tosylate to facilitate the transformation. Convert the alcohol to a tosylate by reacting it with p-toluenesulfonyl chloride (TsCl) in the presence of a base like pyridine. This will form the tosylate ester, which is a good leaving group.

Step 3: Perform the nucleophilic substitution. Treat the tosylate with a bromide ion source, such as sodium bromide (NaBr), to replace the tosylate group with a bromide ion, resulting in the desired alkyl bromide.

Step 4: Consider sustainability. The use of tosylates involves the generation of waste products and may require toxic reagents, which can be less sustainable.

Step 5: Suggest an alternative reagent. Instead of using tosylates, you might use phosphorus tribromide (PBr3) directly on the alcohol to convert it to the bromide, which can be a more sustainable and direct method.

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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 derived from tosyl chloride and are used to convert alcohols into better leaving groups. This transformation enhances the reactivity of alcohols in nucleophilic substitution reactions. The tosylate group is a sulfonate ester, which stabilizes the leaving group during the reaction, facilitating the conversion to other functional groups.

Sustainability in Organic Chemistry

Sustainability in organic chemistry refers to the environmental impact and resource efficiency of chemical processes. Methods that produce hazardous waste, require toxic reagents, or consume excessive energy are often deemed unsustainable. Evaluating the sustainability of a reaction involves considering alternative methods that minimize waste and use safer, renewable resources.

Alternative Reagents

Alternative reagents are substances that can replace traditional reagents in chemical reactions to improve efficiency or reduce environmental impact. For example, using greener solvents or catalysts can lead to more sustainable reactions. In the context of the question, identifying a reagent that can achieve the desired transformation without the drawbacks of tosylates is crucial for developing a more sustainable approach.

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Related Practice

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)

Textbook Question

What is the product of each of the following reactions?

Textbook Question

Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:

a. CH₃CH₂CH₂SCH₂CH₃

Textbook Question

Show how you would convert propan-1-ol to the following compounds using tosylate intermediates. You may use whatever additional reagents are needed.

c. CH₃CH₂CH₂OCH₂CH₃, ethyl proyl ether

d. CH₃CH₂CH₂CN, butyronitrile

Textbook Question

Predict the major products of the following reactions, including stereochemistry where appropriate.

(a) (R)-butan-2-ol + TsCl in pyridine

(b) (S)-2-butyl tosylate + NaBr

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(a) Show how you would affect the following transformation using a tosylate. (b) Why might this not be the most sustainable method? (c) What reagent might you use instead?

Key Concepts

Tosylate Formation

Sustainability in Organic Chemistry

Alternative Reagents

Watch next

(a) Show how you would affect the following transformation using a tosylate.
(b) Why might this not be the most sustainable method?
(c) What reagent might you use instead?