Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter2: Alkanes And Cycloalkanes
Section: Chapter Questions
Problem 2.45P: Gibbs free energy differences between axial-substituted and equatorial-substituted chair...
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Question
What is the most stable chair conformation of the 4-methoxy-1,2-dimethylcyclohexane structure given below ?
![### Stereochemistry and Cyclohexane Conformations: 4-Methoxy-1,2-Dimethylcyclohexane
In this educational segment, we will examine the stereochemistry and conformational analysis of a specific cyclohexane derivative, 4-methoxy-1,2-dimethylcyclohexane. Presented below is both the structural formula and four possible chair conformations of the molecule, labeled A, B, C, and D.
#### Structural Formula
The chemical structure of 4-methoxy-1,2-dimethylcyclohexane is shown at the top of the image. The core cyclohexane ring is substituted with the following groups:
- At position 4: a methoxy group (OCH₃)
- At positions 1 and 2: methyl groups (CH₃)
The stereochemistry indicates that the substituents at positions 1 and 2 (two methyl groups) are in different stereochemical orientations, with one group in equatorial and the other in axial positions depending on the conformation.
#### Chair Conformations
The bottom portion of the image illustrates four different chair conformations (A, B, C, D) for 4-methoxy-1,2-dimethylcyclohexane:
- **Conformation A:** In this conformation, the methoxy group is axial, and the two methyl groups at positions 1 and 2 are both equatorial.
- **Conformation B:** Here, the methoxy group is axial, the methyl group at position 1 is equatorial, and the methyl group at position 2 is axial.
- **Conformation C:** In this arrangement, the methoxy group is equatorial, the methyl group at position 1 is axial, and the methyl group at position 2 is equatorial.
- **Conformation D:** The methoxy group is equatorial, and the two methyl groups at positions 1 and 2 are both axial.
##### Graph Analysis
The image does not contain specific graphs, but the conformations serve as visual aids to help understand the molecule's three-dimensional shape and steric interactions. By examining these conformations, one can determine the most stable arrangement of substituents on the cyclohexane ring. Typically, substituents prefer to be in equatorial positions to minimize 1,3-diaxial interactions, which are more sterically hindered.
### Conclusion](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F1284a8dd-5b62-44ae-ac4b-19fa5317fe3b%2F777e2b29-f242-4e46-b948-e8a975a8b6ec%2F6fzv5om_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Stereochemistry and Cyclohexane Conformations: 4-Methoxy-1,2-Dimethylcyclohexane
In this educational segment, we will examine the stereochemistry and conformational analysis of a specific cyclohexane derivative, 4-methoxy-1,2-dimethylcyclohexane. Presented below is both the structural formula and four possible chair conformations of the molecule, labeled A, B, C, and D.
#### Structural Formula
The chemical structure of 4-methoxy-1,2-dimethylcyclohexane is shown at the top of the image. The core cyclohexane ring is substituted with the following groups:
- At position 4: a methoxy group (OCH₃)
- At positions 1 and 2: methyl groups (CH₃)
The stereochemistry indicates that the substituents at positions 1 and 2 (two methyl groups) are in different stereochemical orientations, with one group in equatorial and the other in axial positions depending on the conformation.
#### Chair Conformations
The bottom portion of the image illustrates four different chair conformations (A, B, C, D) for 4-methoxy-1,2-dimethylcyclohexane:
- **Conformation A:** In this conformation, the methoxy group is axial, and the two methyl groups at positions 1 and 2 are both equatorial.
- **Conformation B:** Here, the methoxy group is axial, the methyl group at position 1 is equatorial, and the methyl group at position 2 is axial.
- **Conformation C:** In this arrangement, the methoxy group is equatorial, the methyl group at position 1 is axial, and the methyl group at position 2 is equatorial.
- **Conformation D:** The methoxy group is equatorial, and the two methyl groups at positions 1 and 2 are both axial.
##### Graph Analysis
The image does not contain specific graphs, but the conformations serve as visual aids to help understand the molecule's three-dimensional shape and steric interactions. By examining these conformations, one can determine the most stable arrangement of substituents on the cyclohexane ring. Typically, substituents prefer to be in equatorial positions to minimize 1,3-diaxial interactions, which are more sterically hindered.
### Conclusion
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