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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2:30 minutes

Problem 50a

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)

Verified step by step guidance

Step 1: Understand the Newman projection. A Newman projection is a way to visualize the conformation of a molecule by looking straight down the bond axis between two atoms. Identify the front carbon (closest to the viewer) and the back carbon (furthest from the viewer). Note the substituents attached to each carbon.

Step 2: Analyze the given Newman projection. Observe the positions of the substituents on the front and back carbons. Pay attention to the labeled substituent and its orientation (e.g., staggered or eclipsed conformation).

Step 3: Determine the direction and degree of rotation. If the problem specifies a clockwise or counterclockwise rotation, apply this rotation to the front carbon while keeping the back carbon fixed. For example, a 120° clockwise rotation means each substituent on the front carbon will move to the next position in a clockwise direction.

Step 4: Redraw the Newman projection after the rotation. Update the positions of the substituents on the front carbon based on the specified rotation. Ensure the back carbon substituents remain unchanged, as the rotation only affects the front carbon.

Step 5: Verify the resulting Newman projection. Check that the labeled substituent is correctly positioned according to the rotation and confirm that the new conformation matches the specified degree and direction of rotation. Ensure the drawing is clear and accurate.

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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 compounds.

Conformational Analysis

Conformational analysis involves studying the different spatial arrangements of atoms in a molecule that can be interconverted by rotation around single bonds. This analysis is essential for predicting the stability of various conformers, as certain arrangements may lead to increased steric hindrance or torsional strain, affecting the molecule's reactivity and properties.

Dihedral Angle

The dihedral angle is the angle between two planes formed by four atoms in a molecule, specifically the angle between the planes of two adjacent bonds. In Newman projections, the dihedral angle is critical for determining the relative positions of substituents and understanding how rotation around a bond can influence the overall conformation and stability of the molecule.

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Related Practice

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.

(b)

Textbook Question

(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.]

(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)

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.]

(l)

Textbook Question

(i) <IMAGE>

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