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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7:18 minutes

Problem 10c,d

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

Verified step by step guidance

Step 1: Begin with propan-1-ol (CH3CH2CH2OH). Convert the hydroxyl group (-OH) into a good leaving group by reacting it with p-toluenesulfonyl chloride (TsCl) in the presence of a base like pyridine. This forms propyl tosylate (CH3CH2CH2OTs).

Step 2: For part (c), to synthesize ethyl propyl ether (CH3CH2CH2OCH2CH3), perform a Williamson ether synthesis. React the propyl tosylate (CH3CH2CH2OTs) with sodium ethoxide (CH3CH2ONa). The ethoxide ion acts as a nucleophile, displacing the tosyl group and forming the ether bond.

Step 3: For part (d), to synthesize butyronitrile (CH3CH2CH2CN), perform a nucleophilic substitution reaction. React the propyl tosylate (CH3CH2CH2OTs) with sodium cyanide (NaCN). The cyanide ion (CN⁻) acts as a nucleophile, displacing the tosyl group and forming the nitrile group.

Step 4: Ensure proper reaction conditions for each step. For the Williamson ether synthesis, use an aprotic solvent like dimethyl sulfoxide (DMSO) to favor the SN2 mechanism. For the nitrile synthesis, also use an aprotic solvent to enhance the nucleophilicity of CN⁻.

Step 5: After each reaction, purify the product using appropriate techniques such as distillation or recrystallization, and confirm the structure of the final compounds using spectroscopic methods like NMR or IR.

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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 alcohols with tosyl chloride (TsCl) in the presence of a base, converting the hydroxyl group into a better leaving group. This transformation is crucial for facilitating nucleophilic substitution reactions, as the tosylate can be displaced by various nucleophiles, allowing for the synthesis of more complex molecules.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule with a nucleophile. In the context of converting propan-1-ol to ethers or nitriles, the tosylate intermediate serves as a substrate for nucleophiles like alkoxides or cyanide ions, which attack the electrophilic carbon, leading to the desired product.

Ether Synthesis

Ether synthesis can be achieved through the reaction of an alkoxide ion with an alkyl halide or tosylate. In this case, the reaction of the tosylate derived from propan-1-ol with an appropriate alkoxide will yield the desired ether, such as CH3CH2CH2OCH2CH3, demonstrating the utility of tosylates in forming ethers efficiently.

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Related Practice

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)