Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
Section4.SE: Something Extra
Problem 35AP: A 1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group...
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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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