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

Constitutional Isomers vs. Stereoisomers

Organic Chemistry

5. Chirality

Constitutional Isomers vs. Stereoisomers

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5:19 minutes

Problem 36g,h

Textbook Question

Which of the following compounds are capable of being resolved into enantiomers?
(g)
(h)

Verified step by step guidance

Step 1: Understand the concept of enantiomers. Enantiomers are stereoisomers that are non-superimposable mirror images of each other. For a compound to be resolved into enantiomers, it must be chiral, meaning it lacks a plane of symmetry and has a stereogenic center (a carbon atom bonded to four different groups).

Step 2: Analyze compound (g). Identify if it contains a stereogenic center by examining each carbon atom and checking if it is bonded to four different groups. If a stereogenic center is present and the molecule lacks symmetry, it is chiral and can be resolved into enantiomers.

Step 3: Analyze compound (h). Similarly, check for the presence of a stereogenic center and determine if the molecule is chiral by ensuring it lacks a plane of symmetry. If these conditions are met, the compound can also be resolved into enantiomers.

Step 4: Consider any additional factors that might affect chirality, such as the presence of double bonds, rings, or meso compounds (which are achiral despite having stereogenic centers due to an internal plane of symmetry).

Step 5: Conclude whether each compound (g) and (h) is capable of being resolved into enantiomers based on the analysis of chirality and the presence of stereogenic centers.

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Key Concepts

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

Enantiomers

Enantiomers are a type of stereoisomer that are non-superimposable mirror images of each other. They typically arise in chiral molecules, which possess at least one chiral center, usually a carbon atom bonded to four different substituents. The presence of enantiomers is crucial in organic chemistry, particularly in the context of pharmaceuticals, as they can exhibit different biological activities.

Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image. A chiral molecule has at least one chiral center, which is often a carbon atom bonded to four distinct groups. Understanding chirality is essential for determining whether a compound can exist as enantiomers and for predicting the behavior of these compounds in biological systems.

Resolution of Enantiomers

Resolution of enantiomers is the process of separating a racemic mixture (a 1:1 mixture of enantiomers) into its individual enantiomers. This can be achieved through various methods, such as crystallization, chromatography, or using chiral reagents. The ability to resolve enantiomers is important in organic synthesis and drug development, as the different enantiomers can have distinct pharmacological effects.

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Related Practice

Textbook Question

How many stereoisomers are possible for the following alkenes?

(d)

Textbook Question

How many stereoisomers are possible for each of the following molecules?

(e)

Textbook Question

Define the relationship between each set of two molecules as chain isomers, positional isomers, functional group isomers, enantiomers, diastereomers, conformational isomers, or identical.

(c)

Textbook Question

If the carbon atom in CH₂Cl₂ were flat, there would be two stereoisomers. The carbon atom in CH₂Cl₂is actually tetrahedral. Make a model of this compound, and determine whether there are any stereoisomers of CH₂Cl₂.

Textbook Question

Make a model and draw a three-dimensional structure for each compound. Then draw the mirror image of your original structure and determine whether the mirror image is the same compound. Label each structure as being chiral or achiral, and label pairs of enantiomers.

(a) cis-1,2-dimethylcyclobutane

(b) trans-1,2-dimethylcyclobutane

Textbook Question

For the molecules shown,

(i) count the number of stereocenters present and

(ii) draw all possible stereoisomers.

(iii) Identify the relationships between stereoisomers as enantiomers or diastereomers.

(c)

Textbook Question

Which of the following compounds are capable of being resolved into enantiomers?

(a) N-ethyl-N-methylaniline

(b) 2-methylpiperidine