On the conformations the cost in k CH 3 3 H 2 5 ~1/1 АЗС 2 chair OH H CH 3 4 ra

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question
**Exercise 3: Conformational Analysis of Cyclohexane Derivatives**

In this exercise, you are provided with a diagram of a cyclohexane molecule with substituents. Your task is to draw the two possible chair conformations for the given isomer and calculate the cost in kcal/mol for each conformation.

**Diagram Details:**

- The central diagram shows a cyclohexane ring with numbered carbon atoms from 1 to 6.
- Substituents are attached as follows:
  - C1: CH₃ (methyl group)
  - C2: H (hydrogen)
  - C3: CH₃ (methyl group)
  - C4: OH (hydroxyl group)
  - C5: H (hydrogen)
  - C6: H₃C (methyl group)
- Two additional chair conformation templates are provided.
- Each carbon in the chair templates is labeled from 1 to 6.

**Instructions:**

1. Use the given cyclohexane ring with substituents to determine steric and torsional strain in different conformations.
2. Draw the two possible chair conformations using the templates provided.
3. Assign substituents to appropriate axial/equatorial positions based on their orientations in the original structure.
4. Calculate the energy cost (in kcal/mol) of each conformation, considering factors like 1,3-diaxial interactions.

This exercise will help you understand the impact of different substitutions on cyclohexane's conformational preferences and the resulting energy differences.
Transcribed Image Text:**Exercise 3: Conformational Analysis of Cyclohexane Derivatives** In this exercise, you are provided with a diagram of a cyclohexane molecule with substituents. Your task is to draw the two possible chair conformations for the given isomer and calculate the cost in kcal/mol for each conformation. **Diagram Details:** - The central diagram shows a cyclohexane ring with numbered carbon atoms from 1 to 6. - Substituents are attached as follows: - C1: CH₃ (methyl group) - C2: H (hydrogen) - C3: CH₃ (methyl group) - C4: OH (hydroxyl group) - C5: H (hydrogen) - C6: H₃C (methyl group) - Two additional chair conformation templates are provided. - Each carbon in the chair templates is labeled from 1 to 6. **Instructions:** 1. Use the given cyclohexane ring with substituents to determine steric and torsional strain in different conformations. 2. Draw the two possible chair conformations using the templates provided. 3. Assign substituents to appropriate axial/equatorial positions based on their orientations in the original structure. 4. Calculate the energy cost (in kcal/mol) of each conformation, considering factors like 1,3-diaxial interactions. This exercise will help you understand the impact of different substitutions on cyclohexane's conformational preferences and the resulting energy differences.
Expert Solution
Step 1

A six-membered ring with 6 tetrahedra naturally assumes a chair conformation as the conformation of lowest energy, which minimizes trans-annular interactions. Knowing this is no substitute for getting a set of models and having a play with them. Now, not only do you have to be able to recognize the conformations, you also have to able to translate that 3D geometry onto the 2D printed page. This is certainly non-trivial.

Chair conformation: A six-membered ring conformation in which atoms 2, 3, 5, and 6 lie in the same plane, atom 1 lies above the plane, and atom 4 lies below the plane.

conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted just by rotations about formally single bonds (refer to figure on single bond rotation).

steps

Step by step

Solved in 4 steps with 3 images

Blurred answer
Knowledge Booster
Spectroanalytical Methods
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY