Answered: Illsutrate the Ring-flipping…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter7: Cycloalkanes

Section: Chapter Questions

Problem 10E: True or False: If you perform a chair flip on cis-1,4-dichlorocyclohexane, the result is still...

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Question

Illsutrate the Ring-flipping interconverts axial and equatorial hydrogens in
cyclohexane ?

Expert Solution

Step 1

Cyclohexane-

Structure is-

In the conformational analysis cyclohexanes, cis and trans isomers are differential based on the position of substituents.
The substituents may or may not be same. Only based on their relative positions in the ring they considered as cis and trans.

These are positions in cyclohexane.

Step 2

Answer of given question-

In isomer A, H₁ is the axial hydrogen and H₂ is equatorial hydrogen.
After flipping equatorial H₂ in A goes to the axial position in B and also H₁ in A goes to equatorial position in B.
So equatorial hydrogens go to the axial position and axial hydrogens go to the equatorial positions after flipping of cyclohexane.
Carbon-hydrogen bonds that are axial in first configuration become equatorial in other or vice versa. But the positions of their ‘up’ or ‘down’ does not change, remains as it is.

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