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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7:20 minutes

Problem 48c,d

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the Newman projection for part c. The front carbon (circle) has substituents Br, H, and CH3. The back carbon (behind the circle) has substituents CH2CH3, H, and H. Identify the spatial arrangement of these groups to determine the connectivity.

Step 2: Convert the Newman projection for part c into a line-angle formula. The front carbon is bonded to Br, H, and CH3, while the back carbon is bonded to CH2CH3 and two H atoms. Draw the structure with the correct bond angles and connectivity.

Step 3: Assign the IUPAC name for part c. Identify the longest carbon chain, determine the substituents, and assign locants based on priority rules (e.g., halogens and alkyl groups). Ensure the name reflects the correct stereochemistry if applicable.

Step 4: Analyze the Newman projection for part d. The front carbon (circle) has substituents CH2CH3, H, and Cl. The back carbon (behind the circle) has substituents CH(CH3)2, H, and CH3. Identify the spatial arrangement of these groups to determine the connectivity.

Step 5: Convert the Newman projection for part d into a line-angle formula. The front carbon is bonded to CH2CH3, H, and Cl, while the back carbon is bonded to CH(CH3)2, H, and CH3. Draw the structure with the correct bond angles and connectivity, and assign the IUPAC name using the same process as in part c.

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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 substituents around the bond, which is crucial for analyzing steric interactions and torsional strain in organic compounds.

Line-Angle Formulas

Line-angle formulas, also known as skeletal structures, are a shorthand way of representing organic molecules. In this format, vertices represent carbon atoms, and lines represent bonds, making it easier to visualize complex structures without explicitly drawing every atom. This method is particularly useful for quickly conveying the structure of larger organic molecules.

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides rules for constructing names based on the structure of the molecule, including the longest carbon chain, functional groups, and substituents. Understanding these rules is essential for accurately identifying and communicating the identity of organic compounds.

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Related Practice

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

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

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.

Textbook Question

Draw the conformer that is present in greatest concentration.

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

Key Concepts

Newman Projections

Line-Angle Formulas

IUPAC Nomenclature

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