Question

H3C CH3 2 HO 1 CH3 3 2-isopropyl-3-methylcyclohexanol There are four cis, trans isomers for 2-isopropyl-3-methylcyclohexanol, where the cis, trans designations of the substituents are made relative to the OH group: • up, up, up (cis,cis) • up, up, down (cis, trans) • up, down, down (trans,cis) • up, down, up (trans, trans) Consider the most stable chair for each of these isomers, and then draw the most stable and least stable isomer based on a comparison of the best chair for each one. • To simplify matters, consider only axial vs equatorial energies of the groups (i.e. do not worry about the interactions between the groups, which in reality is also important). • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • Use \"flat\" representations of rings, not chairs, in your drawing. Most stable Least stable

          H3C
CH3
2
HO
1
CH3
3
2-isopropyl-3-methylcyclohexanol
There are four cis, trans isomers for 2-isopropyl-3-methylcyclohexanol, where the cis, trans
designations of the substituents are made relative to the OH group:
• up, up, up (cis,cis)
• up, up, down (cis, trans)
• up, down, down (trans,cis)
• up, down, up (trans, trans)
Consider the most stable chair for each of these isomers, and then draw the most stable and least
stable isomer based on a comparison of the best chair for each one.
• To simplify matters, consider only axial vs equatorial energies of the groups (i.e. do not
worry about the interactions between the groups, which in reality is also important).
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• You do not have to explicitly draw H atoms.
• Use \"flat\" representations of rings, not chairs, in your drawing.
Most stable
Least stable

H3C
CH3
2
HO
1
CH3
3
2-isopropyl-3-methylcyclohexanol
There are four cis, trans isomers for 2-isopropyl-3-methylcyclohexanol, where the cis, trans
designations of the substituents are made relative to the OH group:
• up, up, up (cis,cis)
• up, up, down (cis, trans)
• up, down, down (trans,cis)
• up, down, up (trans, trans)
Consider the most stable chair for each of these isomers, and then draw the most stable and least
stable isomer based on a comparison of the best chair for each one.
• To simplify matters, consider only axial vs equatorial energies of the groups (i.e. do not
worry about the interactions between the groups, which in reality is also important).
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• You do not have to explicitly draw H atoms.
• Use f̈latr̈epresentations of rings, not chairs, in your drawing.
Most stable
Least stable

Added by Rebecca B.

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