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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2:29 minutes

Problem 53i

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.]
(i) <IMAGE>

Verified step by step guidance

Orient yourself as the 'eyeball' looking directly down the indicated bond. Identify the front carbon (closest to the eye) and the back carbon (furthest from the eye) along the bond axis.

Draw a circle to represent the back carbon atom. The front carbon atom will be represented by a dot in the center of the circle.

Identify the three substituents attached to the front carbon. Arrange them as lines radiating outward from the central dot, spaced at 120° angles. Ensure their positions match the 3D structure of the molecule.

Identify the three substituents attached to the back carbon. Arrange them as lines radiating outward from the edge of the circle, spaced at 120° angles. Ensure their positions match the 3D structure of the molecule.

Double-check the relative positions of all substituents to ensure the Newman projection accurately represents the stereochemistry of the molecule as viewed down the bond.

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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 a bond between two carbon atoms. This representation helps in understanding the spatial arrangement of substituents attached to the carbons, allowing for the analysis of steric interactions and torsional strain in different conformations.

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 crucial 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.

Steric Hindrance

Steric hindrance refers to the repulsion between atoms or groups within a molecule that occurs when they are brought close together. In the context of Newman projections, understanding steric hindrance is essential for evaluating the stability of different conformations, as bulky groups can create unfavorable interactions that influence the preferred conformation of the molecule.

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Related Practice

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)

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

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.]

(l) <IMAGE>

Textbook Question

Draw Newman projections along the C3―C4 bond to show the most stable and least stable conformations of 3-ethyl-2,4,4-trimethylheptane.

Textbook Question

Draw Newman projections of the following molecules viewed from the direction of the blue arrows.

(c)

Textbook Question

For each molecule, draw the Newman projection you would observe if you looked down the C_a - C_b bond in the direction indicated.

(d) <IMAGE>

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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.](i) <IMAGE>

Key Concepts

Newman Projections

Conformational Analysis

Steric Hindrance

Watch next

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.]
(i) <IMAGE>