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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6:02 minutes

Problem 7e,f

Textbook Question

In Problem 5-3, you drew the enantiomers for a number of chiral compounds. Now go back and designate each asymmetric carbon atom as either (R) or (S).
(e) chlorocyclohexane
(f) cis-1,2-dichlorocyclobutane

Verified step by step guidance

Step 1: Understand the problem. You are tasked with assigning the configuration (R or S) to each asymmetric carbon atom in the given compounds: chlorocyclohexane and cis-1,2-dichlorocyclobutane. The images provided are not directly related to the problem but serve as examples of stereochemistry in cyclic compounds.

Step 2: Recall the Cahn-Ingold-Prelog priority rules. To assign R or S configuration, you need to: (a) Assign priorities to the substituents attached to the chiral carbon based on atomic number, (b) Orient the molecule so the lowest priority group is pointing away from you, and (c) Determine the order of the remaining groups (clockwise for R, counterclockwise for S).

Step 3: For chlorocyclohexane, identify the chiral carbon. The chiral carbon is the one bonded to four different groups: a chlorine atom, a hydrogen atom, and two different parts of the cyclohexane ring. Assign priorities based on atomic number (Cl > C > H). Orient the molecule and determine the configuration.

Step 4: For cis-1,2-dichlorocyclobutane, identify the two chiral carbons. Each carbon in the 1,2 positions is bonded to a chlorine atom, a hydrogen atom, and two different parts of the cyclobutane ring. Assign priorities for each chiral carbon (Cl > C > H). Orient the molecule and determine the configuration for each carbon.

Step 5: Verify your assignments by checking the spatial arrangement of the substituents and ensuring the lowest priority group is pointing away. Use the clockwise or counterclockwise rule to finalize the R or S designation for each chiral carbon.

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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. Chiral molecules typically contain one or more asymmetric carbon atoms, which are carbon atoms bonded to four different substituents. This property is crucial in organic chemistry as it affects the behavior of molecules in biological systems and their interactions with other chiral substances.

R and S Nomenclature

The R and S nomenclature system is used to assign configurations to chiral centers in molecules. To determine whether a chiral center is designated as (R) or (S), the substituents attached to the asymmetric carbon are ranked according to their atomic number. The orientation of the highest priority substituents, when viewed from a specific perspective, determines the designation: clockwise for (R) and counterclockwise for (S).

Cyclic Compounds and Stereochemistry

Cyclic compounds, such as cyclohexane and cyclobutane, can exhibit stereochemistry due to the arrangement of substituents around the ring. The presence of substituents in different orientations (cis or trans) can lead to different stereoisomers. Understanding the stereochemistry of cyclic compounds is essential for determining their reactivity and interactions, particularly in the context of chiral centers.

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Related Practice

Textbook Question

Draw a perspective formula for each of the following:

a. (S)-2-chlorobutane

b. (R)-1,2-dibromobutane

Textbook Question

Draw structures for the following:

a. (S)-1-bromo-1-chlorobutane

b. (2R,3R)-2,3-dichloropentane

c. an achiral stereoisomer of 1,2-dimethylcyclohexane

Textbook Question

In Problem 5-3 , you drew the enantiomers for a number of chiral compounds. Now go back and designate each asymmetric carbon atom as either (R) or (S).e. Chlorocyclohexane f. Cis-1,2-dichlorocyclobutane

Textbook Question

3,4-Dimethylpent-1-ene has the formula CH₂=CH—CH(CH₃)—CH(CH₃)₂. When pure (R)-3,4-dimethylpent-1-ene is treated with hydrogen over a platinum catalyst, the product is (S)-2,3-dimethylpentane.

a. Draw the equation for this reaction. Show the stereochemistry of the reactant and the product.

b. Has the chiral center retained its configuration during this hydrogenation, or has it been inverted?

Textbook Question

In Problem 5-3, you drew the enantiomers for a number of chiral compounds. Now go back and designate each asymmetric carbon atom as either (R) or (S).

(c)

(d) 1-bromo-2-methylbutane

Textbook Question

In Problem 5-3, you drew the enantiomers for a number of chiral compounds. Now go back and designate each asymmetric carbon atom as either (R) or (S).

(a)

(b)

Textbook Question

c. The reactant is named (R), but the product is named (S). Does this name change imply a change in the spatial arrangement of the groups around the chiral center? So why does the name switch from (R) to (S)?

Textbook Question

Naproxen is a commercially available anti-inflammatory sold under the name Aleve.

(a) Assign the absolute configuration as R or S.

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