Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 5, Problem 49P

(Use models to solve this problem.)

(a) Write a conformational structure for the most stable conformation of trans-1,2-diethylcyclohexane its minor image.

(b) Are these two molecules superposable?

(c) Are they interconvertible through a chair-chair “flip”?

(d) Repeat the process in pare (a) with cis-1,2-diethylcyclohexane.

(e) Are these structures superposable?

(f) Are they interconvertible?

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(B) Draw two chair conformations of the following substituted cyclohexane and identify the most stable conformation. Clearly show the axial and equatorial bonds.
Consider 1-bromopropane,  CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which ­ CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?
Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3- dimethylcyclohexane, and 1,4-dimethylcyclohexane. (a ) Indicate by a label whether each methyl group is axial or equatorial. (b) For which isomer(s) are the alternative chair conformations of equal stability? (c) For which isomer(s) is one chair conformation more stable than the other?

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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License