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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2:45 minutes

Problem 12a

Textbook Question

Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:
a. CH₃CH₂CH₂SCH₂CH₃

Verified step by step guidance

Step 1: Begin by converting 1-propanol (CH3CH2CH2OH) into a sulfonate ester. This can be achieved by reacting 1-propanol with a sulfonyl chloride, such as p-toluenesulfonyl chloride (TsCl), in the presence of a base like pyridine. This reaction replaces the hydroxyl group (-OH) with a tosyl group (-OTs), forming CH3CH2CH2OTs.

Step 2: The sulfonate ester (CH3CH2CH2OTs) is now a good leaving group, which facilitates substitution reactions. To introduce the desired thiol group (-SCH2CH3), perform a nucleophilic substitution reaction (SN2 mechanism) using ethanethiol (CH3CH2SH) as the nucleophile.

Step 3: In the SN2 reaction, the ethanethiol attacks the carbon attached to the tosyl group in CH3CH2CH2OTs, displacing the tosyl group and forming CH3CH2CH2SCH2CH3. Ensure the reaction is carried out in an appropriate solvent, such as acetone, to favor the SN2 mechanism.

Step 4: After the reaction, purify the product (CH3CH2CH2SCH2CH3) using techniques such as distillation or chromatography to remove any unreacted starting materials and by-products.

Step 5: Confirm the structure of the final product (CH3CH2CH2SCH2CH3) using spectroscopic methods such as NMR or IR to verify the presence of the thiol group and the absence of the tosyl group.

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Key Concepts

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

Sulfonate Esters

Sulfonate esters are derivatives of alcohols where the hydroxyl group (-OH) is replaced by a sulfonate group (-OSO2R). They are important in organic synthesis as they can be converted into various nucleophiles through nucleophilic substitution reactions. This transformation enhances the leaving group ability, facilitating the formation of carbon-carbon bonds or other functional groups.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule with a nucleophile. In the context of sulfonate esters, the sulfonate group acts as a good leaving group, allowing nucleophiles to attack the carbon atom bonded to it. This mechanism is crucial for converting 1-propanol into more complex structures, such as the desired thioether in the question.

Thioether Formation

Thioethers, also known as sulfides, are organic compounds containing a sulfur atom bonded to two alkyl or aryl groups. The formation of thioethers from alcohols typically involves the reaction of a sulfonate ester with a thiol (R-SH). Understanding this reaction is essential for synthesizing the target compound from 1-propanol, as it illustrates how to create carbon-sulfur bonds effectively.

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Related Practice

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

(a) Show how you would affect the following transformation using a tosylate.

(b) Why might this not be the most sustainable method?

Textbook Question

What is the product of each of the following reactions?

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.