ORGANIC CHEMISTRY-NEXTGEN+BOX (1 SEM.)
ORGANIC CHEMISTRY-NEXTGEN+BOX (1 SEM.)
4th Edition
ISBN: 9781119760986
Author: Klein
Publisher: WILEY
bartleby

Concept explainers

bartleby

Videos

Question
Book Icon
Chapter 6.6, Problem 6.41P
Interpretation Introduction

Interpretation:

The most stable chair conformation for the given compound has to be drawn.

Concept Introduction:

When a compound contains a cyclohexane ring in it, then there are three possibilities of conformations.  They are chair, boat and twist-boat.  Among these three conformations of cyclohexane ring, the most stable one is the chair conformation.

ORGANIC CHEMISTRY-NEXTGEN+BOX (1 SEM.), Chapter 6.6, Problem 6.41P , additional homework tip  1

In the above structure, there are twelve substituents that can be placed.  Among the twelve, six are axial substituents and six are equatorial substituents.  The axial substituents can be represented as shown below,

ORGANIC CHEMISTRY-NEXTGEN+BOX (1 SEM.), Chapter 6.6, Problem 6.41P , additional homework tip  2

The equatorial substituents can be represented as,

ORGANIC CHEMISTRY-NEXTGEN+BOX (1 SEM.), Chapter 6.6, Problem 6.41P , additional homework tip  3

To draw a group in a correct configuration, we have to understand what is coming towards us and what is going away from us (wedge and dash bonds).

ORGANIC CHEMISTRY-NEXTGEN+BOX (1 SEM.), Chapter 6.6, Problem 6.41P , additional homework tip  4

For drawing the other chair conformation, a ring flip has to be done.  Ring flipping makes the skeleton as shown below,

ORGANIC CHEMISTRY-NEXTGEN+BOX (1 SEM.), Chapter 6.6, Problem 6.41P , additional homework tip  5

During this ring flip from one chair conformation to another, all the substituents present in axial position goes to equatorial position and vice-versa.

ORGANIC CHEMISTRY-NEXTGEN+BOX (1 SEM.), Chapter 6.6, Problem 6.41P , additional homework tip  6

The most stable conformation among the two chair conformations can be found by looking into the bulky groups that are present in the ring.  The chair conformation which has the bulky group in equatorial position will be the more stable one as there wont be steric interaction.  If the bulky group is present in axial position, then there will be axial-axial interaction, which makes the conformation less stable.  In simple words, we can say that the bulky group will prefer to be in equatorial position.

Blurred answer
Students have asked these similar questions
Wavelength (nm) I'm not sure what equation I can come up with other than the one generated with my graph. Can you please show me the calculations that were used to find this equation? Give an equation that relates energy to wavelength. Explain how you arrived at your equation. Wavelength Energy (kJ/mol) (nm) 350 341.8 420 284.8 470 254.5 530 225.7 580 206.3 620 192.9 700 170.9 750 159.5 Energy vs. Wavelength (Graph 1) 400 350 y=-0.4367x+470.82 300 250 200 150 100 50 O 0 100 200 300 400 500 600 700 800 Energy (kJ/mol)
6. For the following molecules: draw Lewis dot-structures; use VSEPR method to determine geometries of the following molecules/ions. Are the central atoms in these molecules/ions considered of normal valency, or are they hypervalent? (please read paragraph 2.6) a) BrF3 (6 points) b) BrF4 c) IF₂ 4
None
Knowledge Booster
Background pattern image
Chemistry
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
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY