H3C. H3C. 3 HO ČH3 3-isopropyl-4-methylcyclohexanol There are four cis,trans isomers for 3-isopropyl-4-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)

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
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Chapter7: Cycloalkanes
Section: Chapter Questions
Problem 15E
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Use flat representation of rings, not chair in the drawing 

[References]
napter 2
H3C.
H3C.
HO.
CH3
3-isopropyl-4-methylcyclohexanol
There are four cis, trans isomers for 3-isopropyl-4-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 impo
• 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
C P
Transcribed Image Text:[References] napter 2 H3C. H3C. HO. CH3 3-isopropyl-4-methylcyclohexanol There are four cis, trans isomers for 3-isopropyl-4-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 impo • 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 C P
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