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

5. Chirality

R and S Configuration

Organic Chemistry

5. Chirality

R and S Configuration

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Problem 24f

Textbook Question

Prioritize the substituents at each chiral center and then, by comparing them to the models you created in Section 6.3.2, label the absolute configuration as R or S
(f)

Verified step by step guidance

Step 1: Identify the chiral center in the molecule. A chiral center is a carbon atom bonded to four different substituents. In the given structure, the carbon atom bonded to the hydroxyl group (OH), the oxygen atom in the ring, the ring itself, and the wedge/dash bond is the chiral center.

Step 2: Assign priorities to the substituents attached to the chiral center based on the Cahn-Ingold-Prelog (CIP) priority rules. These rules state that the substituent with the highest atomic number gets the highest priority. For this molecule: (1) The oxygen atom in the ring has the highest priority, (2) The hydroxyl group (OH) is next, (3) The ring structure is third, and (4) The hydrogen atom (not shown explicitly but implied by the dash bond) has the lowest priority.

Step 3: Orient the molecule so that the lowest priority group (hydrogen) is pointing away from you (on the dashed bond). This orientation is crucial for determining the absolute configuration.

Step 4: Trace the path from the highest priority substituent (1) to the second (2) and then to the third (3). If the path is clockwise, the configuration is R. If the path is counterclockwise, the configuration is S.

Step 5: Compare the result of your analysis to the models and examples provided in Section 6.3.2 to confirm the absolute configuration as R or S.

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Key Concepts

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

Chirality

Chirality refers to the geometric 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 molecule's stereochemistry. Understanding chirality is essential for labeling configurations as R or S.

Cahn-Ingold-Prelog Priority Rules

The Cahn-Ingold-Prelog (CIP) priority rules are a set of guidelines used to assign priority to substituents attached to a chiral center. According to these rules, substituents are ranked based on the atomic number of the atoms directly attached to the chiral center, with higher atomic numbers receiving higher priority. This ranking is fundamental for determining the absolute configuration of chiral centers.

R and S Configuration

The R and S configuration system is used to describe the spatial arrangement of substituents around a chiral center. After assigning priorities to the substituents, the configuration is determined by observing the orientation of the highest priority substituent when the lowest priority is oriented away from the viewer. If the sequence of priorities is clockwise, the configuration is labeled as R (rectus), and if counterclockwise, it is labeled as S (sinister).

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Related Practice

Textbook Question

In Chapter 12, we introduce the S_N2 reaction, a nucleophilic substitution reaction that proceeds with inversion. Confirm that inversion has occurred in each of the following examples by determining the absolute configuration of the chiral center in the reactants and products.

(a)

Textbook Question

Assign the absolute stereochemistry for each of the following molecules.

(e)

Textbook Question

Assign the absolute stereochemistry for each of the following molecules.

(f)

Textbook Question

Prioritize the substituents at each chiral center and then, by comparing them to the models you created in Section 6.3.2, label the absolute configuration as R or S.

(d)

Textbook Question

What is the configuration of each of the asymmetric centers in the following compounds?

Textbook Question

Indicate whether each of the following structures is (R)-2-chlorobutane or (S)-2-chlorobutane:

Textbook Question

Name the isomers you drew in Problem 52.

Textbook Question

Chloramphenicol is a broad-spectrum antibiotic that is particularly useful against typhoid fever. What is the configuration of each of its asymmetric centers?

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Prioritize the substituents at each chiral center and then, by comparing them to the models you created in Section 6.3.2, label the absolute configuration as R or S(f)

Key Concepts

Chirality

Cahn-Ingold-Prelog Priority Rules

R and S Configuration

Watch next

Prioritize the substituents at each chiral center and then, by comparing them to the models you created in Section 6.3.2, label the absolute configuration as R or S
(f)