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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4:37 minutes

Problem 36a,b,c

Textbook Question

Which of the following compounds are capable of being resolved into enantiomers?
(a) N-ethyl-N-methylaniline
(b) 2-methylpiperidine
(c) 1-methylpiperidine

Verified step by step guidance

Step 1: Understand the concept of enantiomers. Enantiomers 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 or other atom bonded to four different groups).

Step 2: Analyze compound (a) N-ethyl-N-methylaniline. This compound contains a nitrogen atom bonded to three groups (ethyl, methyl, and a phenyl group). However, nitrogen inversion (a rapid flipping of the lone pair on nitrogen) prevents the isolation of enantiomers in most cases unless the nitrogen is part of a rigid structure. Therefore, this compound is not resolvable into enantiomers.

Step 3: Analyze compound (b) 2-methylpiperidine. This compound has a nitrogen atom in a six-membered ring and a methyl group attached to the second carbon. The nitrogen atom undergoes inversion, and the molecule does not have a stereogenic center. Thus, it is not resolvable into enantiomers.

Step 4: Analyze compound (c) 1-methylpiperidine. This compound has a nitrogen atom in a six-membered ring and a methyl group attached to the nitrogen. Similar to the previous cases, the nitrogen undergoes inversion, and the molecule lacks a stereogenic center. Therefore, it is not resolvable into enantiomers.

Step 5: Conclude that none of the given compounds (a, b, or c) are capable of being resolved into enantiomers due to the lack of chirality or the presence of nitrogen inversion.

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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 an asymmetric carbon atom. The presence of enantiomers is crucial in organic chemistry as they can exhibit different biological activities and properties, making their identification important in fields like pharmaceuticals.

Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image. A chiral molecule usually has at least one carbon atom bonded to four different substituents, leading to two distinct configurations. Understanding chirality is essential for determining whether a compound can exist as enantiomers.

Resolution of Enantiomers

Resolution of enantiomers is the process of separating a racemic mixture into its individual enantiomers. This is important in organic synthesis and drug development, as different enantiomers can have vastly different effects in biological systems. Techniques such as chiral chromatography or the use of chiral reagents are commonly employed for this purpose.

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Related Practice

Textbook Question

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

(g)

(h)

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

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(a)

Textbook Question

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(f)

Textbook Question

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(b)

Textbook Question

Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror image for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice.Build molecular models of any of these examples that seem difficult to youe. Chlorocyclohexanef. Cis-1,2-dichlorocyclobutane

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Which of the following compounds are capable of being resolved into enantiomers? (a) N-ethyl-N-methylaniline (b) 2-methylpiperidine (c) 1-methylpiperidine

Key Concepts

Enantiomers

Chirality

Resolution of Enantiomers

Watch next

Which of the following compounds are capable of being resolved into enantiomers?
(a) N-ethyl-N-methylaniline
(b) 2-methylpiperidine
(c) 1-methylpiperidine