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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6:37 minutes

Problem 58b

Textbook Question

Starting with (R)-1-deuterio-1-propanol, how could you prepare
b. (S)-1-deuterio-1-methoxypropane?

Verified step by step guidance

Identify the starting material: (R)-1-deuterio-1-propanol. This compound has a hydroxyl (-OH) group attached to the first carbon, which is also chiral due to the presence of a deuterium (D) atom.

Plan the reaction sequence: To convert the hydroxyl group (-OH) into a methoxy group (-OCH₃), you need to perform a substitution reaction. However, the stereochemistry must also invert from (R) to (S), which suggests the use of an SN2 reaction mechanism.

Step 1: Convert the hydroxyl group (-OH) into a good leaving group. This can be achieved by reacting (R)-1-deuterio-1-propanol with a reagent like p-toluenesulfonyl chloride (TsCl) in the presence of a base (e.g., pyridine) to form the corresponding tosylate (R)-1-deuterio-1-propyl tosylate.

Step 2: Perform an SN2 reaction to replace the tosylate group with a methoxy group (-OCH₃). React the tosylate intermediate with sodium methoxide (NaOCH₃) in methanol. The SN2 mechanism will invert the stereochemistry, converting the (R)-configuration to the (S)-configuration.

Verify the product: The final product is (S)-1-deuterio-1-methoxypropane, which has the desired methoxy group and the correct (S)-stereochemistry at the chiral center.

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Key Concepts

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

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In this question, understanding the difference between (R) and (S) configurations is crucial, as it involves the manipulation of chiral centers to achieve the desired stereoisomer. The Cahn-Ingold-Prelog priority rules are typically used to assign these configurations.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions are fundamental organic reactions where a nucleophile replaces a leaving group in a molecule. In the context of preparing (S)-1-deuterio-1-methoxypropane from (R)-1-deuterio-1-propanol, a nucleophilic substitution can be employed, typically involving the conversion of the alcohol to a better leaving group followed by reaction with a methoxide ion.

Deuteration

Deuteration refers to the substitution of hydrogen atoms in a molecule with deuterium, an isotope of hydrogen. This process is significant in the question as it involves maintaining the deuterium label while transforming (R)-1-deuterio-1-propanol into (S)-1-deuterio-1-methoxypropane. Understanding how deuterium affects molecular properties and reactivity is essential for predicting the outcome of the reaction.

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