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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2:16 minutes

Problem 12b

Textbook Question

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

Verified step by step guidance

Step 1: Begin by converting 1-propanol into a sulfonate ester. This is achieved by reacting 1-propanol with a sulfonyl chloride, such as p-toluenesulfonyl chloride (TsCl), in the presence of a base like pyridine. The hydroxyl group (-OH) of 1-propanol is replaced with a tosyl group (-OTs), forming propyl tosylate.

Step 2: The sulfonate ester (propyl tosylate) is now a good leaving group due to the stability of the tosylate ion. This makes it suitable for substitution reactions. Choose the appropriate nucleophile depending on the desired product. For example, if you want to form an alkyl halide, use a halide ion (e.g., Cl⁻, Br⁻, or I⁻) as the nucleophile.

Step 3: Perform the nucleophilic substitution reaction (SN2 mechanism). The nucleophile attacks the carbon attached to the tosyl group, displacing the tosylate ion and forming the desired product. Ensure the reaction conditions are suitable for SN2, such as using a polar aprotic solvent like acetone or DMSO.

Step 4: If the desired compound requires further functional group modification, perform additional reactions. For example, if you need an alkene, you can eliminate the tosylate group using a strong base (e.g., NaOH or KOH) under heat to induce an E2 elimination reaction.

Step 5: Verify the structure of the final product using spectroscopic techniques such as NMR or IR to confirm the successful conversion of 1-propanol into the desired compound.

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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 intermediates in organic synthesis because they can undergo nucleophilic substitution reactions, allowing for the conversion of alcohols into more reactive species. This transformation enhances the electrophilicity of the carbon atom bonded to the sulfonate group, facilitating further reactions.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule by a nucleophile. In the context of sulfonate esters, the sulfonate group acts as a good leaving group, allowing nucleophiles to attack the carbon atom. This reaction can follow either an SN1 or SN2 mechanism, depending on the structure of the substrate and the conditions, influencing the stereochemistry and rate of the reaction.

Conversion of Alcohols to Alkyl Halides

The conversion of alcohols to alkyl halides is a common transformation in organic chemistry, often achieved through the formation of sulfonate esters. This process allows for the substitution of the hydroxyl group with a halide, enabling the synthesis of various alkyl halides. This transformation is significant for creating more reactive intermediates that can participate in further chemical reactions, such as coupling or elimination.

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