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

Drawing Newman Projections

Organic Chemistry

4. Alkanes and Cycloalkanes

Drawing Newman Projections

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3:12 minutes

Problem 22b

Textbook Question

Using the Newman projections shown, draw each molecule in its line-angle drawing with all hydrogens and substituents shown. [Carbon b is behind carbon a in these structures.] Wedges and dashes should be used to indicate whether a substituent is coming out of, or going into, the plane of the page.
(b)

Verified step by step guidance

Step 1: Understand the Newman projection. A Newman projection is a way to visualize the spatial arrangement of atoms around a bond. In this case, carbon 'a' is in the front, and carbon 'b' is behind. Identify the substituents attached to each carbon and their relative positions (e.g., staggered or eclipsed).

Step 2: Translate the Newman projection into a 3D perspective. For carbon 'a' (front carbon), draw the substituents radiating outward from the center. Use wedges to indicate substituents coming out of the plane of the page and dashes for substituents going into the plane of the page.

Step 3: For carbon 'b' (back carbon), position its substituents behind carbon 'a' in the drawing. Ensure the substituents are correctly aligned based on the Newman projection (e.g., staggered or eclipsed).

Step 4: Connect the two carbons with a single bond. Ensure the spatial arrangement of substituents matches the Newman projection. Double-check the orientation of wedges and dashes to accurately represent the 3D structure.

Step 5: Add all hydrogens and substituents explicitly in the line-angle drawing. Verify that the final structure matches the Newman projection and includes all necessary details, such as bond angles and substituent positions.

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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 the spatial arrangement of substituents around the bond, which is crucial for analyzing steric interactions and torsional strain in organic molecules.

Line-Angle Drawings

Line-angle drawings, also known as skeletal structures, are a shorthand way of representing organic molecules. In these drawings, carbon atoms are represented by the ends and intersections of lines, while hydrogen atoms are often omitted for simplicity. Understanding how to convert Newman projections into line-angle drawings is essential for accurately depicting molecular structures.

Wedges and Dashes

Wedges and dashes are used in structural representations to indicate the three-dimensional orientation of substituents on a molecule. A wedge (solid triangle) shows that a substituent is coming out of the plane of the page, while a dash (dashed line) indicates that it is going into the plane. This notation is vital for conveying the stereochemistry of a molecule accurately.

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Related Practice

Textbook Question

For rotation about the C-3---C-4 bond of 2-methylhexane, do the following:

a. Draw the Newman projection of the most stable conformer.

b. Draw the Newman projection of the least stable conformer.

Textbook Question

c. Draw Newman projections of the two conformers of the trans isomer.

d. Which of the conformers predominates at equilibrium?

Textbook Question

Given the following structures, show the Newman projection that would result from looking down the indicated bond in the direction shown. [Orient yourself as if you were the eyeball looking down the bond. Some of the examples have been partially completed for you to fill in the rest.]

(k) <IMAGE>

Textbook Question

(j) <IMAGE>

Textbook Question

Using the Newman projections shown, draw each molecule in its line-angle drawing with all hydrogens and substituents shown. [Carbon b is behind carbon a in these structures.] Wedges and dashes should be used to indicate whether a substituent is coming out of, or going into, the plane of the page.

(d)

Textbook Question

Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman projection. [One substituent has been labeled for you.]

(a)

Textbook Question

Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman projection. [One substituent has been labeled for you.]

(d)

Textbook Question

Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman projection. [One substituent has been labeled for you.]

(h)

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