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 17CTQ
Interpretation Introduction

Interpretation: The structure of cis-1, 3-dimethylcyclohexane needs to be drawn in the chair conformation and the same molecule needs to be drawn 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 17CTQ , additional homework tip  1

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

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 17CTQ , 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.

During the flipping, no bond is break. The numbering in the chair form is represented as follows:

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 17CTQ , additional homework tip  3

During ring flipping, mirror image of the chair conformation is formed.

It is represented as follows:

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 17CTQ , additional homework tip  4

Now, the ring flipping with groups attached can be represented as follows;

  Organic Chemistry: A Guided Inquiry, Chapter 7, Problem 17CTQ , additional homework tip  5

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Students have asked these similar questions
Draw cis and trans chair conformations for 1,4- dimethylcyclohexane. Comment on what happens when a "chair - chair flip" occurs and draw both chair forms and circle the most favorable conformation. Also, comment on the types of strain present.
c) Draw the most stable chair conformation for each of the following cyclohexanes. Now, "flip" the ring and redraw the molecule in the higher energy form. i) chlorocyclohexane ii) cis-1-chloro-2-methylcyclohexane iii) trans-1-methyl-3-propylcyclohexane
Draw the Newman projection so that it corresponds to the molecule and conformation shown when viewed down the red bond in the direction of the arrow. HC H HN H
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