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

1:13 minutes

Problem 10b

Textbook Question

For each of the following molecules, draw one 3-D representation at only the necessary atoms (that is, the ones with four different atoms/groups attached).
(b)

Verified step by step guidance

Identify the stereocenter in the molecule. A stereocenter is an atom (usually carbon) that is attached to four different groups. In the given molecule, the carbon atom bonded to the chlorine (Cl), a methyl group (CH3), a hydrogen (H), and the carbonyl group (C=O) is the stereocenter.

Understand the 3-D representation of the stereocenter. The stereocenter is represented using wedge and dash bonds to indicate the spatial arrangement of the groups. A wedge bond indicates a group coming out of the plane towards the viewer, while a dash bond indicates a group going behind the plane away from the viewer.

Assign priorities to the four groups attached to the stereocenter based on the Cahn-Ingold-Prelog (CIP) priority rules. The group with the highest atomic number gets the highest priority. In this case: Cl > C=O > CH3 > H.

Position the lowest priority group (hydrogen) on the dash bond (going behind the plane). Arrange the other groups (Cl, CH3, and C=O) around the stereocenter based on their priorities.

Draw the 3-D representation of the stereocenter with the correct spatial arrangement of the groups. Ensure the wedge and dash bonds are used appropriately to depict the stereochemistry of the molecule.

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.

Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image. A chiral molecule typically has a carbon atom bonded to four different substituents, leading to two distinct enantiomers. Understanding chirality is crucial for predicting the behavior of molecules in biological systems, as enantiomers can have different effects.

3-D Molecular Representation

3-D molecular representation is a way to depict the spatial arrangement of atoms in a molecule. This representation is essential for visualizing chirality, as it shows how different groups are oriented in three-dimensional space. Techniques such as wedge-and-dash notation or ball-and-stick models are commonly used to illustrate these spatial relationships.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the given molecule, the presence of a chlorine atom and a carbonyl group (C=O) indicates specific reactivity and properties. Identifying functional groups is key to understanding the behavior and classification of organic compounds.

Watch next

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

Start learning

Related Videos

Related Practice

Textbook Question

Draw all possible stereoisomers for each of the following. Indicate those compounds for which no stereoisomers are possible.

e. 1-bromo-4-chlorocyclohexane

f. 1,2-dimethylcyclopropane

Textbook Question

In contrast to Assessment 6.63, the following compounds should be easily separable using standard methods. Why?

Textbook Question

For the compound 1-ethyl-3-isopropylcyclopentane

Textbook Question

For each of the following molecules, draw one 3-D representation at only the necessary atoms (that is, the ones with four different atoms/groups attached).

(a)

Multiple Choice

Which of the following describes stereoisomers?

Textbook Question

Give the relationships between the following pairs of structures. The possible relationships are as follows: same compound, cis-trans isomers, constitutional (structural) isomers, and not isomers (different molecular formula).

(a) CH₃CH₂CH₂CH₃ and (CH₃)₃CH

(b) CH₂=CH–CH₂Cl and CHCl=CH–CH₃

Textbook Question

For each pair of structures, determine whether they represent different compounds or a single compound.

Textbook Question

Give the relationship between the following pairs of structures. The possible relationships are:

same compound

constitutional isomers (structural isomers)

cis-trans isomers

not isomers (different molecular formula)

(a)

(b)