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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Problem 52d

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>

Verified step by step guidance

Identify the bond in the given structure that you are instructed to look down. This is typically specified in the problem (e.g., C1-C2 or C2-C3). Ensure you understand which atoms are connected by this bond.

Orient the molecule in your mind or on paper so that you are looking directly down the specified bond. The front carbon (closer to you) and the back carbon (further away) will form the basis of the Newman projection.

Determine the substituents attached to the front carbon. These substituents will be represented as three groups radiating out from the center of the front carbon in the Newman projection.

Determine the substituents attached to the back carbon. These substituents will also be represented as three groups radiating out from the center of the back carbon in the Newman projection, but they will be positioned behind the front carbon.

Draw the staggered Newman projection by arranging the substituents on the front and back carbons such that the groups on the back carbon are positioned in the gaps between the groups on the front carbon. This arrangement minimizes torsional strain and represents the staggered conformation.

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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 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.

Staggered vs. Eclipsed Conformations

In a Newman projection, staggered conformations occur when the substituents on adjacent carbons are positioned as far apart as possible, minimizing steric hindrance. In contrast, eclipsed conformations have substituents aligned with each other, leading to increased repulsion and higher energy states. Recognizing these conformations is essential for predicting the stability of different molecular arrangements.

Dihedral Angle

The dihedral angle is the angle between two planes formed by four atoms in a molecule, specifically the angle between the bonds on the front and back carbon atoms in a Newman projection. This angle is critical for determining the conformation of the molecule, as it influences the interactions between substituents and can affect the overall energy and reactivity of the compound.

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Related Practice

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>

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.]

(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

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

(c)

(d)

Textbook Question

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

c. 3,3-dimethylhexane, viewed along the C-3---C-4 bond

Textbook Question

For the following molecule, draw the Newman projection (around the 2,3-bond) with a dihedral angle of 180° between the bromine and hydrogen.

Textbook Question

Conformational studies on ethane-1,2-diol (HOCH₂–CH₂OH) have shown the most stable conformation about the central C―C bond to be the gauche conformation, which is 9.6 kJ/mol (2.3 kcal/mol) more stable than the anti conformation. Draw Newman projections of these conformers, and explain this curious result.

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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>

Key Concepts

Newman Projections

Staggered vs. Eclipsed Conformations

Dihedral Angle

Watch next

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>