We saw that the energy cost of an axial methyl is 1.8 kcal/mol; therefore, we might expect cis-1,3-dimethylcyclohexane to have chair conformations with a difference in totalenergy of 3.6 kcal/mol.    1. Is the calculated energy difference in cis-1,3-dimethylcyclohexane higher or lower than expected? Propose an explanation for the difference between the expected energy difference and the calculated energy difference in cis-1,3-dimethylcyclohexane. (Limit your answer to 10 words or fewer)   2. Recall that an axial methyl is typically worth around 1.8 kcal/mol. Propose an explanation for the difference in the value above for 1-methyltetrahydropyran. (Limit your answer to 10 words or less)

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

 

We saw that the energy cost of an axial methyl is 1.8 kcal/mol; therefore, we might expect cis-1,3-dimethylcyclohexane to have chair conformations with a difference in totalenergy of 3.6 kcal/mol. 

 

1. Is the calculated energy difference in cis-1,3-dimethylcyclohexane higher or lower than expected? Propose an explanation for the difference between the expected energy difference and the calculated energy difference in cis-1,3-dimethylcyclohexane. (Limit your answer to 10 words or fewer)

 

2. Recall that an axial methyl is typically worth around 1.8 kcal/mol. Propose an explanation for the difference in the value above for 1-methyltetrahydropyran. (Limit your answer to 10 words or less)

 

3. Would you expect the difference in strain energy between the chairs of 5-methyl-1,3-dioxane to be greater than or less than that of 1-methyltetrahydropyran? Is it GREATER THAN or LESS THAN? 

Expert Solution
steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Knowledge Booster
Alkanes and Cycloalkanes
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.
Similar questions
  • SEE MORE QUESTIONS
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