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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5:59 minutes

Problem 9c,d

Textbook Question

What stereoisomers do the following reactions form?
c.
d.

Verified step by step guidance

Analyze the first reaction: The alcohol reacts with HCl under heat. This is a substitution reaction where the hydroxyl group (-OH) is replaced by a chlorine atom (-Cl). The reaction proceeds via a carbocation intermediate, which can lead to rearrangements and the formation of stereoisomers depending on the stability of the carbocation.

Step 1 for reaction c: The hydroxyl group is protonated by HCl, forming water as a leaving group. This generates a carbocation intermediate. The carbocation is tertiary, which is stable and does not undergo rearrangement.

Step 2 for reaction c: The chloride ion (Cl⁻) attacks the carbocation, leading to the formation of the product. Since the carbocation is planar, the attack can occur from either side, resulting in a racemic mixture of stereoisomers (R and S configurations).

Analyze the second reaction: The alcohol reacts with PCl₃ in the presence of pyridine. This is a substitution reaction where the hydroxyl group (-OH) is replaced by a chlorine atom (-Cl). The reaction proceeds via an SN2 mechanism, which involves a backside attack and inversion of configuration.

Step 1 for reaction d: The hydroxyl group is activated by PCl₃, forming a good leaving group (phosphoryl intermediate). Pyridine acts as a base to facilitate the reaction. The chloride ion (Cl⁻) performs a backside attack, leading to the inversion of configuration at the stereocenter. The product will have the opposite stereochemistry compared to the starting material.

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Key Concepts

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

Stereoisomerism

Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of those atoms. This can lead to different physical and chemical properties. The two main types of stereoisomers are enantiomers, which are non-superimposable mirror images, and diastereomers, which are not mirror images of each other.

Reaction Mechanisms

Understanding reaction mechanisms is crucial for predicting the products of chemical reactions, including stereoisomers. A reaction mechanism outlines the step-by-step process by which reactants transform into products, detailing the formation and breaking of bonds. Key factors in these mechanisms include the type of reaction (e.g., substitution, elimination) and the stereochemical outcomes based on the orientation of reactants.

Chirality

Chirality is a property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. Chiral centers, typically carbon atoms bonded to four different substituents, are crucial in determining the stereochemistry of a compound. The presence of chirality in a reaction can lead to the formation of enantiomers, which can have significantly different biological activities.

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Related Practice

Textbook Question

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.

(g)