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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2:37 minutes

Problem 58a

Textbook Question

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

Verified step by step guidance

Identify the stereochemistry of the starting material, (R)-1-deuterio-1-propanol. The (R) configuration indicates the specific spatial arrangement of the substituents around the chiral center.

To convert the (R)-1-deuterio-1-propanol to its enantiomer, (S)-1-deuterio-1-propanol, you need to invert the stereochemistry at the chiral center. This can be achieved through a two-step process: conversion to an intermediate and subsequent inversion.

Step 1: Convert the alcohol group (-OH) into a good leaving group. This can be done 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. The tosylate group is an excellent leaving group.

Step 2: Perform an SN2 reaction with a nucleophile (e.g., hydroxide ion, OH⁻) to replace the tosylate group with a hydroxyl group. The SN2 mechanism involves a backside attack, which inverts the stereochemistry at the chiral center, resulting in (S)-1-deuterio-1-propanol.

Finally, confirm the stereochemistry of the product using spectroscopic methods (e.g., NMR or optical rotation) to ensure the desired (S)-configuration has been achieved.

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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 context, it is crucial to understand the difference between enantiomers, which are molecules that are mirror images of each other, such as (R)- and (S)-1-deuterio-1-propanol. The ability to manipulate these configurations is essential for synthesizing specific stereoisomers.

Chiral Centers

A chiral center, often a carbon atom, is bonded to four different substituents, leading to non-superimposable mirror images. In the case of 1-deuterio-1-propanol, the chiral center's configuration determines whether the molecule is in the (R) or (S) form. Understanding how to identify and modify chiral centers is key to synthesizing the desired stereoisomer.

Reactions for Synthesis

Various chemical reactions can be employed to convert one stereoisomer into another, such as inversion reactions or specific chiral catalysts. For example, using a suitable reagent that selectively reacts with the (R)-1-deuterio-1-propanol can lead to the formation of (S)-1-deuterio-1-propanol. Familiarity with these synthetic pathways is essential for achieving the desired product.

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Related Practice

Textbook Question

Predict the product of the following sulfonylation reactions.

(c)

Textbook Question

Complete the following multistep syntheses using tosylate formation as one of the steps. The optimum number of steps for each synthesis is shown.

(c)

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)

Textbook Question

Write the appropriate reagent over each arrow.

Multiple Choice

Which of the following syntheses would be best to make the given molecule?

Textbook Question

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

Textbook Question

Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:

Textbook Question

Show how you would convert propan-1-ol to the following compounds using tosylate intermediates. You may use whatever additional reagents are needed.

a. 1-bromopropane