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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1:43 minutes

Problem 63g

Textbook Question

What is the major product(s) of each of the following reactions?
g.

Verified step by step guidance

Step 1: Analyze the starting material. The molecule is a cyclopentanol derivative with a hydroxyl (-OH) group and a methyl group attached to the ring. The hydroxyl group is in the axial position.

Step 2: Understand the role of TsCl/pyridine. Tosyl chloride (TsCl) reacts with the hydroxyl group in the presence of pyridine to convert it into a tosylate (-OTs) group. This step makes the hydroxyl group a better leaving group.

Step 3: Consider the stereochemistry of the tosylation reaction. The tosylate group will retain the stereochemistry of the original hydroxyl group, as this reaction does not invert the configuration.

Step 4: Examine the second reagent, NaCN. Sodium cyanide (NaCN) is a nucleophile that will perform an SN2 reaction, displacing the tosylate group. Since SN2 reactions proceed with inversion of configuration, the cyanide group (-CN) will attach to the carbon in the equatorial position.

Step 5: Predict the major product. The major product will be a cyclopentane ring with a cyanide group (-CN) in the equatorial position and a methyl group in the axial position, due to the stereochemical inversion during the SN2 reaction.

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Key Concepts

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

Alcohol Activation

In organic chemistry, alcohols can be converted into better leaving groups through activation. In this reaction, TsCl (tosyl chloride) is used in the presence of pyridine to convert the alcohol (-OH) into a tosylate, which is a more reactive species. This transformation facilitates subsequent nucleophilic substitution reactions.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, after the alcohol is converted to a tosylate, NaCN (sodium cyanide) acts as the nucleophile, attacking the carbon atom bonded to the tosylate and resulting in the formation of a nitrile (R-C≡N).

Formation of Nitriles

Nitriles are organic compounds containing a cyano group (-C≡N) and are often formed through nucleophilic substitution reactions involving alkyl halides or activated alcohols. The reaction of the tosylate with NaCN leads to the formation of a nitrile, which can be useful in various synthetic applications, including the synthesis of amines and carboxylic acids.

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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)