Q8.4 Structure CH3 CH3 ВЕ .C -E D I II What substituent is positioned at B on Structure II? O -H O -CH3 Q8.5 Structure CH3 CH3 В ВЕ .C A -E H3C A I II What substituent is positioned at C on Structure II? O H O -CH3 Q8.6 Structure CH3 CH3 B E A H3C A F, F I II What substituent is positioned at E on Structure II? O -H -CH3
Q8.4 Structure CH3 CH3 ВЕ .C -E D I II What substituent is positioned at B on Structure II? O -H O -CH3 Q8.5 Structure CH3 CH3 В ВЕ .C A -E H3C A I II What substituent is positioned at C on Structure II? O H O -CH3 Q8.6 Structure CH3 CH3 B E A H3C A F, F I II What substituent is positioned at E on Structure II? O -H -CH3
Chemistry
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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:### Q8.4 Structure
This question involves the transformation of a cyclohexane derivative into two different structures (I and II). The starting molecule is a cyclohexane ring with two methyl (CH₃) groups.
#### Diagrams:
- **Structure I**: Represents the cyclohexane chair conformation with substituents labeled A, B, C, D, E, and F.
- **Structure II**: Depicts the flipping of the chair conformation, altering the positions of the substituents.
**Question**: What substituent is positioned at B on Structure II?
- ○ -H
- ○ -CH₃
---
### Q8.5 Structure
This question also involves a cyclohexane derivative transforming into structures I and II. The focus is on a different substituent location compared to Q8.4.
#### Diagrams:
- **Structure I**: Displays the cyclohexane chair conformation, with substituents labeled A through F.
- **Structure II**: Shows the result of the conformational change (chair flip).
**Question**: What substituent is positioned at C on Structure II?
- ○ -H
- ○ -CH₃
---
### Q8.6 Structure
This question follows the same transformation theme but examines another substituent position on the cyclohexane ring.
#### Diagrams:
- **Structure I**: Displays the cyclohexane chair arrangement, with substituents labeled A through F.
- **Structure II**: Illustrates the conformational change due to chair flipping.
**Question**: What substituent is positioned at E on Structure II?
- ○ -H
- ○ -CH₃
Transcribed Image Text:```markdown
### Q8 Conformational Analysis of Cycloalkanes
In this question, you will look at the conformations of the following molecule:
**Molecule Diagram:**
The diagram shows a cyclohexane ring with various substituents. The substituents include methyl groups. Two conformations are depicted:
- **Conformation I and Conformation II**: Both structures feature the cyclohexane ring with different orientations of the substituents labeled A through F.
---
### Energy Costs for Interactions in Alkane Conformers:
| Interaction | Computed Energy Cost (kJ/mol)⁺ |
|---------------------------------|--------------------------------|
| H↔H eclipsed | 3.8 |
| H↔CH₃ eclipsed | 4.8 |
| CH₃↔CH₃ eclipsed | 12.6 |
| CH₃↔CH(CH₃)₂ gauche | 3.7 |
| H↔CH(CH₃)₂ gauche | (0.0) |
| H↔CH(CH₃)₂ eclipsed | 3.1 |
| CH₃↔CH(CH₃)₂ gauche | 3.6 |
| CH₃↔CH(CH₃)₂ eclipsed | 17.3 |
| H↔C(CH₃)₃ eclipsed | 2.8* |
| CH₃↔C(CH₃)₃ gauche | 13.6 |
| CH₃↔C(CH₃)₃ eclipsed | 18.7 |
| H↔e₁ eclipsed | 6.7 |
| I↔CH₃ gauche | 1.2 |
| I↔CH₃ eclipsed | 15.5 |
⁺ Values computed with Gaussian09 using B3LYP/6-31G(d) for structure optimization and B3LYP/6-311+G(2df,3p) for conformation energy. Calculations were performed in the gas phase (no solvent).
* Note: This result for t-butyl is peculiar since the value is less than that for isopropyl, but an explanation will be provided in office hours.
---
###
Expert Solution
Step 1
Equatorial conformation is more stable than axial confirmation.
The stable chair conformation of the given compound will be that in which maximum no. of CH3 groups will be at equatorial position. Thus the stable confirmation will be:
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