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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3:10 minutes

Problem 11c

Textbook Question

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

Verified step by step guidance

Identify the molecule and the specific bond you are viewing along the direction of the blue arrow. Newman projections are typically used to visualize the conformation around a single bond, so it's crucial to know which bond you are focusing on.

Determine the front and back carbon atoms along the bond you are viewing. The front carbon is the one closest to you, and the back carbon is the one further away.

Draw a circle to represent the back carbon atom. This circle will help you visualize the spatial arrangement of the substituents attached to the back carbon.

Draw three lines radiating from the center of the circle to represent the substituents attached to the back carbon. These lines should be evenly spaced at 120 degrees apart, forming a 'Y' shape within the circle.

Draw the front carbon atom as a point in front of the circle. From this point, draw three lines radiating outward to represent the substituents attached to the front carbon. These lines should also be spaced at 120 degrees apart, forming a 'Y' shape. Ensure that the substituents on the front carbon do not overlap with those on the back carbon, as this will help visualize the staggered or eclipsed conformation.

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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 perspective 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, or conformers, can interconvert through such rotations, affecting the molecule's energy and stability. Understanding conformational isomerism is essential for predicting the most stable conformation of a molecule, which is often depicted using Newman projections.

Steric Hindrance

Steric hindrance occurs when atoms or groups within a molecule are positioned in such a way that they physically impede each other's space, leading to increased energy and decreased stability. In Newman projections, steric hindrance is visualized by the proximity of substituents on adjacent carbons, influencing 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.]

(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.]

(i) <IMAGE>

Textbook Question

(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

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>

Textbook Question

(b) <IMAGE>

Textbook Question

Looking down the indicated bond, show the three most stable conformations and choose the one that is most stable. Be sure that the first Newman projection you show is the one you see initially (before rotation). [Why should none of your three Newman projections show eclipsed conformations?]

(b) <IMAGE>

Textbook Question

For each of the following structures, which staggered Newman projection skeleton from Assessment 3.51 should you draw first to show what is seen when looking down the indicated bond?

(d) <IMAGE>

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

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.
(c)