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 106k(iii,iv)

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)

Verified step by step guidance

Identify the functional group present in the molecule. The given structure is a cyclohexanol derivative with a tertiary alcohol group.

For condition (iii) with SOCl₂ and NEt₃: Recognize that SOCl₂ (thionyl chloride) is used to convert alcohols into alkyl chlorides. The NEt₃ (triethylamine) acts as a base to neutralize the HCl formed during the reaction.

Predict the reaction mechanism for condition (iii): The hydroxyl group (OH) of the alcohol will be replaced by a chlorine atom, resulting in the formation of a tertiary alkyl chloride.

For condition (iv) with 1. TsCl, Et₃N 2. NaCN: Understand that TsCl (tosyl chloride) converts the alcohol into a tosylate, which is a good leaving group. Et₃N (triethylamine) acts as a base to facilitate this conversion.

Predict the reaction mechanism for condition (iv): The tosylate intermediate will undergo nucleophilic substitution with NaCN, resulting in the formation of a nitrile group, replacing the tosylate group.

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Key Concepts

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

Thionyl Chloride (SOCl₂) Reactivity

Thionyl chloride is a reagent commonly used in organic chemistry for converting alcohols into alkyl chlorides. The reaction proceeds through the formation of an intermediate that facilitates the substitution of the hydroxyl group with a chlorine atom. Understanding this mechanism is crucial for predicting the products of reactions involving SOCl₂.

Triethylamine (NEt₃) as a Base

Triethylamine is a non-nucleophilic base often used in organic reactions to deprotonate acids or to neutralize generated acids. In the context of reactions with SOCl₂, NEt₃ helps to promote the formation of the desired alkyl chloride by removing protons and stabilizing the reaction environment. Recognizing its role is essential for understanding the overall reaction mechanism.

TsCl and Nucleophilic Substitution

TsCl, or tosyl chloride, is used to convert alcohols into better leaving groups, facilitating nucleophilic substitution reactions. When combined with a base like Et₃N, it forms a tosylate intermediate, which can then react with nucleophiles such as NaCN. This concept is vital for predicting the products of the sequential reactions outlined in the question.

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