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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5:34 minutes

Problem 52d

Textbook Question

Complete the structure of each of these so that it matches the (R) or (S) configuration associated with the name.
(d)

Verified step by step guidance

Analyze the structure of suvorexant provided in the image. Identify the stereocenter marked with the (R) configuration.

Recall the Cahn-Ingold-Prelog priority rules to assign priorities to the substituents attached to the stereocenter. Assign priorities based on atomic number and connectivity.

Orient the molecule so that the lowest priority group is pointing away from you (into the plane of the paper). This is typically represented as a dashed bond.

Determine the order of the remaining three substituents (1, 2, 3) around the stereocenter. If the sequence is clockwise, the configuration is (R); if counterclockwise, it is (S).

Adjust the substituents or bonds in the structure to ensure the stereocenter matches the (R) configuration as specified in the problem.

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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. Molecules that possess chirality have at least one chiral center, typically a carbon atom bonded to four different substituents. This property is crucial in organic chemistry as chiral molecules can exhibit different biological activities, making it essential to determine their (R) or (S) configurations.

R and S Configuration

The (R) and (S) designations are used to describe the absolute configuration of chiral centers in a molecule. The Cahn-Ingold-Prelog priority rules are applied to assign priorities to the substituents attached to the chiral carbon. If the sequence of priority decreases in a clockwise direction, the configuration is (R); if it decreases counterclockwise, it is (S). This classification is vital for understanding the stereochemistry of compounds.

Stereoisomerism

Stereoisomerism is a form of isomerism where molecules have the same molecular formula and connectivity but differ in the spatial arrangement of atoms. This includes both geometric isomers (cis/trans) and optical isomers (enantiomers). Understanding stereoisomerism is essential in organic chemistry, particularly in drug design, as different stereoisomers can have vastly different pharmacological effects.

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Related Practice

Textbook Question

Given the name, draw the structure of the following compounds.

(e) (3R,5S)-5-chloro-3-isopropylcycloheptene

Textbook Question

Using IUPAC rules, name the following molecules.

(c)

Textbook Question

Using IUPAC rules, name the following molecules.

(e)

Textbook Question

Name the following alkynes according to the IUPAC rules of nomenclature.

(b)

Textbook Question

Complete the structure of each of these so that it matches the (R) or (S) configuration associated with the name.

(e)

Textbook Question

Name the following alkynes according to the IUPAC rules of nomenclature.

(d)

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)

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