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

Previous problemNext problem

3:10 minutes

Problem 31e,f

Textbook Question

Draw the enantiomer, if any, for each structure.
(e)
(f)

Verified step by step guidance

Step 1: Understand the concept of enantiomers. Enantiomers are stereoisomers that are non-superimposable mirror images of each other. They occur when a molecule has a chiral center, typically a carbon atom bonded to four different groups.

Step 2: Analyze structure (e). The molecule contains a chiral center at the carbon bonded to H, Br, and the two different alkene groups. To draw the enantiomer, reverse the wedge and dash bonds for the H and Br groups. This will create the mirror image of the original structure.

Step 3: Analyze structure (f). The molecule is a bicyclic compound with a methyl group and hydrogens attached. Check for chirality by identifying if the substituents on the bridgehead carbon are arranged in a way that makes the molecule non-superimposable on its mirror image.

Step 4: If structure (f) is chiral, draw its enantiomer by flipping the spatial arrangement of the substituents (e.g., reverse the positions of the methyl group and hydrogen on the chiral center). Ensure the mirror image is non-superimposable.

Step 5: Verify the enantiomers by confirming that the original structure and its mirror image cannot be superimposed. This ensures the correctness of the drawn enantiomers.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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 molecules that contain a chiral center, which is a carbon atom bonded to four different substituents. Understanding enantiomers is crucial for predicting the behavior of molecules in biological systems, as they can have vastly different properties and activities.

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 distinct groups, creating two different configurations. Recognizing chirality is essential for determining whether a compound has enantiomers and for understanding its potential interactions in biological contexts.

Cyclic and Acyclic Structures

Cyclic structures are closed-loop molecules, while acyclic structures are open-chain molecules. The presence of double bonds and the arrangement of substituents in acyclic structures can influence their chirality. In the context of the provided question, analyzing the structure's connectivity and substituents is vital for identifying any potential enantiomers.

Watch next

Master Determining when molecules are different. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

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

(c)

Textbook Question

Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror 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 you

(a)

(b)

Textbook Question

Draw the stereoisomers of the following amino acids. Indicate pairs of enantiomers and pairs of diastereomers.

Textbook Question

Which of the following pairs of compounds could be separated by recrystallization or distillation?

a. meso-tartaric acid and (±)-tartaric acid (HOOC—CHOH—CHOH—COOH)

Textbook Question

1-Bromo-2-methylcyclopentane has four pairs of diastereomers. Draw the four pairs.

Textbook Question

Draw all possible stereoisomers for each of the following:

b. 2-bromo-4-chlorohexane