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

Newman Projections

Organic Chemistry

4. Alkanes and Cycloalkanes

Newman Projections

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1:38 minutes

Problem 60

Textbook Question

Which of the following conformers of isobutyl chloride is the most stable?

Verified step by step guidance

Step 1: Analyze the Newman projections provided for conformers A, B, and C. These projections represent the molecule viewed along the C-C bond axis, showing the spatial arrangement of substituents around the bond.

Step 2: Identify the bulky groups in the molecule. In isobutyl chloride, the CH3 groups are bulky, and their spatial arrangement will influence the stability of the conformers due to steric hindrance.

Step 3: Evaluate the positions of the substituents in each conformer. The most stable conformer will minimize steric hindrance by placing bulky groups as far apart as possible, typically in an anti-periplanar arrangement.

Step 4: Consider the interaction between the chlorine atom and the CH3 groups. Chlorine is less bulky than CH3, but its position relative to the CH3 groups can also affect stability due to dipole-dipole interactions.

Step 5: Determine which conformer has the least steric hindrance and the most favorable arrangement of substituents. This conformer will be the most stable.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Conformational Analysis

Conformational analysis involves studying the different spatial arrangements of a molecule that can be interconverted by rotation around single bonds. In the case of isobutyl chloride, the stability of its conformers is influenced by steric interactions and torsional strain, which can be evaluated through Newman projections.

Steric Hindrance

Steric hindrance refers to the repulsion between atoms that occurs when they are brought close together, affecting the stability of molecular conformations. In the conformers of isobutyl chloride, bulky groups like the isobutyl group can create steric clashes, making certain conformations less stable than others.

Torsional Strain

Torsional strain arises from the eclipsing interactions between atoms or groups in a molecule when they are aligned in a way that increases electron repulsion. In the context of isobutyl chloride, conformers that minimize torsional strain by adopting staggered arrangements are generally more stable than those with eclipsed conformations.

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Related Practice

Textbook Question

Which of the following structures represent the same compound? Which ones represent different compounds?

(f)

Textbook Question

Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentane along the C2―C3 bond.

a. Place C2 in front, represented by three bonds coming together in a Y shape, and C3 in back, represented by a circle with three bonds pointing out from it.

b. Define the dihedral angle as the angle between the methyl group on the front carbon and the ethyl group on the back carbon.

Textbook Question

Calculate the dihedral angle (θ) for the conformations shown.

(c)

Multiple Choice

What is the dihedral angle between two gauche groups in a Newman projection?

Textbook Question

Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentane along the C2―C3 bond.

c. Begin your graph at the 0° dihedral angle and begin to turn the front carbon.

Textbook Question

Draw a graph, similar to Figure 3-11, of the torsional energy of 2-methylbutane as it rotates about the C2—C3 bond.

Textbook Question

Draw a graph, similar to Figure 3-9, of the torsional strain of 2-methylpropane as it rotates about the bond between C1 and C2. Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.

Textbook Question

Calculate the dihedral angle (θ) for the conformations shown.

(a)

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