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

4. Alkanes and Cycloalkanes

Axial vs Equatorial

Organic Chemistry

4. Alkanes and Cycloalkanes

Axial vs Equatorial

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2:07 minutes

Problem 52b

Textbook Question

This is a Newman projection of a substituted cyclohexane.
b. Draw the equivalent structure using wedge and dash notation on a cyclohexane hexagon.

Verified step by step guidance

Identify the front and back carbon atoms in the Newman projection. The front carbon is the one closer to the viewer, and the back carbon is the one further away.

Determine the substituents on the front carbon. In the Newman projection, the front carbon has a bromine (Br) atom, two hydrogen (H) atoms, and is connected to the back carbon.

Determine the substituents on the back carbon. The back carbon has a methyl group (CH₃), two hydrogen (H) atoms, and is connected to the front carbon.

Draw the cyclohexane ring using a hexagon. Place the substituents on the appropriate carbon atoms using wedge and dash notation. Wedges indicate bonds coming out of the plane towards the viewer, and dashes indicate bonds going behind the plane.

Position the bromine and methyl group on the cyclohexane ring. Since the bromine is on the front carbon, it will be on one of the axial or equatorial positions, and the methyl group on the back carbon will be similarly positioned. Ensure the correct stereochemistry is represented.

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Key Concepts

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

Newman Projections

Newman projections are a way to visualize the conformation of a molecule by looking straight down the bond connecting two carbon atoms. This representation helps in understanding steric interactions and torsional strain between substituents on adjacent carbons, which is crucial for predicting the stability of different conformations in cyclic compounds like cyclohexane.

Wedge and Dash Notation

Wedge and dash notation is a method used to depict three-dimensional structures of molecules on a two-dimensional surface. Solid wedges represent bonds that project out of the plane towards the viewer, while dashed lines indicate bonds that extend behind the plane. This notation is essential for accurately representing the spatial arrangement of substituents in cyclohexane derivatives.

Cyclohexane Conformation

Cyclohexane can adopt several conformations, with the chair conformation being the most stable due to minimized steric strain. Understanding the different conformations, including axial and equatorial positions of substituents, is vital for predicting the reactivity and stability of substituted cyclohexanes, as seen in the question's context.

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