Question: Draw the two possible chair conformations for cis-1,3-dimethylcyclohexane. Which conformation, if either, is more stable?
The two possible chair conformations are as follows:
The more stable conformation is that in which the methyl groups are at equatorial positions.
The cis conformation is obtained when two locations have axial (it may be up or down) substitution or equatorial substitution. Trans conformation is in contrast to cis.
The stable chair conformation is that in which the bulky groups are at equatorial positions.
The cis-1,3-dimethylcyclohexane can be shown by substituting the two-methyl group at the axial position or two methyl groups at equatorial positions.
Least stable conformation
Most stable conformation
Here, ax represents axial and eq represents equatorial.
The more stable conformation of cis-1,3-dimethylcyclohexane is the one in which two methyl groups are at equatorial positions. In this conformation, there is minimum electron cloud distortion.
Question: Glucose is a simple sugar with five substituents bonded to a six-membered ring.
a. Using a chair representation, draw the most stable arrangement of these substituents on the six-membered ring.
b. Convert this representation into one that uses a hexagon with wedges and dashed wedges.
c. Draw a constitutional isomer of glucose.
d. Draw a stereoisomer that has an axial OH group on one carbon.
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