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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2:58 minutes

Problem 53k

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.]
(k) <IMAGE>

Verified step by step guidance

Step 1: Identify the bond you are looking down. In this case, the bond is between the central carbon (attached to the chlorine atom) and the adjacent carbon (attached to the hydroxyl group and the aldehyde group). Orient yourself as if you are the eyeball looking down this bond in the direction indicated by the arrow.

Step 2: Determine the groups attached to the front carbon (the carbon closest to the 'eyeball'). The front carbon has three substituents: a hydroxyl group (-OH), an aldehyde group (-CHO), and a single bond to the central carbon.

Step 3: Determine the groups attached to the rear carbon (the carbon furthest from the 'eyeball'). The rear carbon has three substituents: a chlorine atom (Cl), a methyl group (-CH3), and a single bond to the front carbon.

Step 4: Draw the Newman projection. Represent the front carbon as a dot and the rear carbon as a circle. Arrange the substituents of the front carbon around the dot and the substituents of the rear carbon around the circle. Ensure the spatial arrangement reflects the correct stereochemistry (e.g., staggered or eclipsed conformation).

Step 5: Label each substituent clearly in the Newman projection. For example, place the hydroxyl group, aldehyde group, and bond to the rear carbon around the dot, and place the chlorine atom, methyl group, and bond to the front carbon around the circle. Double-check the orientation to ensure accuracy.

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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 the bond connecting two carbon atoms. This representation helps in understanding the spatial arrangement of atoms or groups attached to these carbons, allowing chemists to analyze steric interactions and torsional strain in different conformations.

Conformational Analysis

Conformational analysis involves studying the different spatial arrangements of a molecule that can be achieved 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.

Line-Angle Structures

Line-angle structures, or skeletal formulas, are a shorthand representation of organic molecules where vertices represent carbon atoms and lines represent bonds. This notation simplifies the drawing of complex molecules by omitting hydrogen atoms attached to carbons, making it easier to visualize the overall structure and connectivity, especially in larger organic compounds.

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Related Practice

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

Textbook Question

Draw a potential-energy diagram for rotation about the C-2---C-3 bond of pentane through 360°, starting with the least stable conformer.

Textbook Question

For rotation about the C-3---C-4 bond of 2-methylhexane, do the following:

a. Draw the Newman projection of the most stable conformer.

b. Draw the Newman projection of the least stable conformer.

Textbook Question

c. Draw Newman projections of the two conformers of the trans isomer.

d. Which of the conformers predominates at equilibrium?

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.]

(j) <IMAGE>

Textbook Question

Using the Newman projections shown, draw each molecule in its line-angle drawing with all hydrogens and substituents shown. [Carbon b is behind carbon a in these structures.] Wedges and dashes should be used to indicate whether a substituent is coming out of, or going into, the plane of the page.

(b)

Textbook Question

(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.]

(a)

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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.](k) <IMAGE>

Key Concepts

Newman Projections

Conformational Analysis

Line-Angle Structures

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.]
(k) <IMAGE>