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 Summary

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions Summary

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4:45 minutes

Problem 96

Textbook Question

A graduate student attempted the following reaction and did not isolate the expected product.
(a) What product did they isolate?
(b) What reagent should they have used instead to get their desired product?

Verified step by step guidance

Examine the starting material, which is a cyclohexanol with a hydroxyl group (OH) attached to the cyclohexane ring. The hydroxyl group is in the axial position.

Consider the reagent used, HCl, which is typically used for converting alcohols to alkyl chlorides via an SN1 or SN2 mechanism. However, the reaction did not proceed as expected.

Identify the issue with the reaction conditions. The presence of HCl suggests an SN1 mechanism, which requires a stable carbocation intermediate. The cyclohexanol structure may not favor carbocation formation due to steric hindrance or lack of resonance stabilization.

Determine the product that was isolated. Since the expected product was not obtained, the reaction may have led to a rearrangement or an alternative reaction pathway, possibly resulting in a different halogenated compound or no reaction.

Suggest an alternative reagent that could facilitate the desired transformation. Consider using thionyl chloride (SOCl2) or phosphorus tribromide (PBr3) for a more effective conversion of alcohols to alkyl halides, as these reagents can proceed via an SN2 mechanism without requiring carbocation formation.

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Key Concepts

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

Alcohol Reactivity

Alcohols can undergo various reactions, including substitution and elimination. In the presence of strong acids like HCl, alcohols can be converted into alkyl halides through a substitution reaction. Understanding the reactivity of alcohols is crucial for predicting the products of reactions involving them.

Mechanism of Substitution Reactions

Substitution reactions can occur via two main mechanisms: SN1 and SN2. SN1 involves the formation of a carbocation intermediate, while SN2 is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. The choice of mechanism affects the product formed and is essential for determining the expected outcome of the reaction.

Reagent Selection

The choice of reagent can significantly influence the reaction pathway and the product obtained. In this case, using HCl may lead to unexpected products due to competing reactions or rearrangements. Understanding which reagents promote desired reactions is vital for achieving specific synthetic goals in organic chemistry.