4. Ring Inversion of Substituted Cyclohexane 4.1 Two Chair Conformations of Substituted Cyclohexane Rings ● When Ring Flipping Occurs If a substituent is initially in the axial position, after ring flipping it will be in the position (and vice-versa). equatorial 4 Connectivity does NOT change. Substituents stay on the same side of the ring that they started on! The cis-trans relationships do NOT change (cis groups stay cis and trans groups stay trans.) 5 5 H3C Pown 3 6 3 6 CH3 CH3 2 2 pour eq vors the chair conformations. dorth and CH3 DOOR in energy than the 6 down 3 1 5 32 N S CH₂ On up on 02 2 CH₂
4. Ring Inversion of Substituted Cyclohexane 4.1 Two Chair Conformations of Substituted Cyclohexane Rings ● When Ring Flipping Occurs If a substituent is initially in the axial position, after ring flipping it will be in the position (and vice-versa). equatorial 4 Connectivity does NOT change. Substituents stay on the same side of the ring that they started on! The cis-trans relationships do NOT change (cis groups stay cis and trans groups stay trans.) 5 5 H3C Pown 3 6 3 6 CH3 CH3 2 2 pour eq vors the chair conformations. dorth and CH3 DOOR in energy than the 6 down 3 1 5 32 N S CH₂ On up on 02 2 CH₂
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...
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Transcribed Image Text:4. Ring Inversion of Substituted Cyclohexane
4.1 Two Chair Conformations of Substituted Cyclohexane Rings
boat conformation is 30
hair conformation. Thus, the equilibrium favors the chair conformations.
_kJ/mol higher
●
●
When Ring Flipping Occurs
If a substituent is initially in the axial position, after ring flipping it will be in the
position (and vice-versa).
equatorial
4
5
5
Connectivity does NOT change.
Substituents stay on the same side of the ring that they started on!
The cis-trans relationships do NOT change (cis groups stay cis and trans groups stay
trans.)
H3C
Pown
6
3
3
6
CH3
1
CH3
2
1
2
eq
I I
CH3
H
180N
-I
6
in energy than the
down
ax
CH₂ On
up
on C
1
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