Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 7, Problem 11E

(a)

Interpretation Introduction

Interpretation: The one which changes during a chair flip in case of cyclohexane and the one which remains the same needs to be explained.

Concept Introduction: Chair conformation is the most stable conformation of cyclohexane. It is represented as follows:

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 11E , additional homework tip  1

Here, the substituted groups in the chair conformation are represented as follows:

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 11E , additional homework tip  2

The groups showing in straight upward and downward directions are axial, and the groups bend slightly right or left are equatorial.

The axial and equatorial groups are represented in the chair conformation as A and E:

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 11E , additional homework tip  3

(b)

Interpretation Introduction

Interpretation: The change in the group that is up and in axial position in the cyclohexane needs to be explained after the chair flip.

Concept Introduction: Chair conformation is the most stable conformation of cyclohexane. It is represented as follows:

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 11E , additional homework tip  4

Here, the substituted groups in the chair conformation are represented as follows:

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 11E , additional homework tip  5

The groups showing in straight upward and downward directions are axial and the groups bend slightly right or left are equatorial.

The axial and equatorial groups are represented in the chair conformation as A and E:

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 11E , additional homework tip  6

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Consider 1,2-dimethylcyclohexane.a. Draw structures for the cis and trans isomers using a hexagon for the six-membered ring.b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?d. Which isomer, cis or trans, is more stable and why?
Consider 1,2-dimethylcyclohexane. a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered ring. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d.Which isomer, cis or trans, is more stable and why?
Please answer A,B and C
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