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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3:04 minutes

Problem 11a

Textbook Question

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

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Identify the carbon-carbon bond that the blue arrow is pointing towards. This will be the axis of rotation for your Newman projection.

Determine the groups attached to the front carbon (the carbon closest to the viewer) and the back carbon (the carbon furthest from the viewer).

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

Arrange the substituents around the front carbon as three lines radiating from the center dot. These lines should be spaced 120 degrees apart.

Arrange the substituents around the back carbon as three lines radiating from the circle. These lines should also be spaced 120 degrees apart, but staggered relative to the front carbon's substituents.

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Key Concepts

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

Newman Projection

A Newman projection is a way of drawing a molecule to show the conformation of a carbon-carbon bond. It is viewed along the axis of the bond, with the front carbon represented by a dot and the back carbon by a circle. This projection helps visualize the spatial arrangement of substituents around the bond, which is crucial for understanding steric interactions and conformational isomerism.

Conformational Isomerism

Conformational isomerism refers to the different spatial arrangements of atoms that result from rotation around a single bond. These isomers, also known as conformers, can interconvert through simple rotations. Understanding conformational isomerism is essential for analyzing the stability and reactivity of molecules, as different conformations can have significantly different energies and properties.

Steric Hindrance

Steric hindrance occurs when atoms or groups within a molecule are positioned such that they physically impede each other's space, leading to increased energy and decreased stability. In Newman projections, steric hindrance is often visualized by the proximity of substituents on adjacent carbons. Recognizing steric hindrance is important for predicting the most stable conformations and understanding reaction mechanisms.

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Related Practice

Textbook Question

Convert each Newman projection to the equivalent line–angle formula, and assign the IUPAC name. g.

(g)

(h)

Textbook Question

Convert each Newman projection to the equivalent line–angle formula, and assign the IUPAC name.

(a)

(b)

Textbook Question

Draw a Newman projection, similar to Figure 3-25 down the C1—C6 bond in the equatorial conformation of methylcyclohexane. Show that the equatorial methyl group is also anti to C5. (Using your models will help.)

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Textbook Question

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

(b)

Textbook Question

Convert the following Newman projections to skeletal structures and name them.

Textbook Question

Draw all the staggered and eclipsed conformers that result from rotation about the C-2-C-3 bond of pentane.

Textbook Question

Using Newman projections, draw the most stable conformer for each of the following:

b. 3-methylhexane, viewed along the C-3----C-4 bond

Textbook Question

Using Newman projections, draw the most stable conformer for each of the following:

a. 3-methylpentane, viewed along the C-2---C-3 bond

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

Key Concepts

Newman Projection

Conformational Isomerism

Steric Hindrance

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