H3C. H3C OH 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 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. H3C OH 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 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

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter7: Cycloalkanes

Section: Chapter Questions

Problem 15E

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