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

Previous problemNext problem

Problem 21d

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>

Verified step by step guidance

Step 1: Understand the concept of a Newman projection. A Newman projection is a way to visualize the spatial arrangement of atoms or groups around a specific bond in a molecule. It involves looking directly down the axis of a bond, typically between two carbon atoms, and representing the front and back atoms as circles with substituents radiating outward.

Step 2: Identify the Cₐ - Cᵦ bond in the molecule. Locate the two carbon atoms (Cₐ and Cᵦ) that form the bond you are observing. Ensure you understand the direction indicated in the problem, as this determines which atom is in the front and which is in the back in the Newman projection.

Step 3: Determine the substituents attached to both Cₐ and Cᵦ. For the front carbon (Cₐ), identify the three groups or atoms attached to it. Similarly, for the back carbon (Cᵦ), identify its three substituents. These will be represented in the Newman projection.

Step 4: Draw the Newman projection. Represent the front carbon (Cₐ) as a dot and the back carbon (Cᵦ) as a circle. Draw the substituents of Cₐ radiating outward from the dot and the substituents of Cᵦ radiating outward from the circle. Ensure the spatial arrangement reflects the actual geometry of the molecule (e.g., staggered or eclipsed conformations).

Step 5: Label the substituents clearly. Indicate the identity of each substituent (e.g., H, CH₃, Cl) and ensure the projection accurately represents the molecule's conformation as viewed down the Cₐ - Cᵦ bond in the specified direction.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

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, allowing for the analysis of steric interactions and torsional strain. By drawing the front carbon as a circle and the back carbon as a larger circle, one can depict the relative positions of the attached groups.

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 understanding the stability of various conformers, as certain arrangements may lead to increased steric hindrance or torsional strain. By evaluating these conformations, chemists can predict the most stable forms of a molecule and their reactivity.

Steric Hindrance

Steric hindrance refers to the repulsion between bulky groups in a molecule that can affect its stability and reactivity. When substituents are positioned close to each other, they can create strain, making certain conformations less favorable. Understanding steric hindrance is essential when drawing Newman projections, as it influences the preferred conformations and the overall energy of the molecule.

Watch next

Master Introduction to Drawing Newman Projections with a bite sized video explanation from Johnny

Start learning

Related Videos

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.]

(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

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

(c)

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>

Textbook Question

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

(c)

(d)

Show more practices