CH3 OH H3C `CH3 2-isopropyl-5-methylcyclohexanol There are four cis,trans isomers for 2-isopropyl-5-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.

CH3 OH H3C `CH3 2-isopropyl-5-methylcyclohexanol There are four cis,trans isomers for 2-isopropyl-5-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.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry

Section4.SE: Something Extra

Problem 62AP: Alcohols undergo an oxidation reaction to yield carbonyl compounds on treatment with CrO3. For...

See similar textbooks

Similar questions

cis-1, 2-Dimethylcyclobutane is less stable than its trans isomer, but cis-l, 3-dimethylcyclobutane is more stable than its trans isomer. Draw the most stable conformations of both, and explain.
Draw (1R,2S,3R)-1bromo-3-fluoro-2-propyl cyclohexane in 2D form
Rank the following groups in order of decreasing priority. a. – COOH, – H, – NH2, – OH b. – H, – CH3, – Cl, – CH2CI c. -CH2CH3, -CH3, -H, -CH(CH3)2 d. – CH = CH2, – CH3, – C ≡ CH, – H
What value is closest to the internal C-C-C bond angle of cyclohexane? Group of answer choices 90o 100o 110o 120o
1) Draw the molecule to which the Newman plot below belongs. 2) a) Draw the Newman projection of the most unstable and stable conformations based on the C2-C3 carbons of butane. b) Draw the most stable conformation of cis-1-methyl-3-ethylcyclohexane. 3) Which of the following molecules are structural isomers with each other?
Give the relationships between the following pairs of structures (a), (c), (d), (e). The possible relationships are: same compound, constitutional isomer, cis-trans isomers, not isomers (different molecular formula). 2-35 Give the relation isomers, constitutional (structural) isomers, (a) CH₂CH₂CH₂CH3 and (CH3)3CH (c) (e) CH CH CH₁ and CH₂ and CH₂ CH, (d) CH3 CH₂ CH₂ CH₂-CH₂ and CH₂CH3 CH3 C=CH₂ CH3 and CH3. CH₂-CH
Draw 1,2,3,4,5,6-hexachlorocyclohexane with a. all the chloro groups in axial positions. b. all the chloro groups in equatorial positions.
1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Draw the alternative chair conformation of lindane and again label which chlorine atoms are axial and which are equatorial.
What is the most stable chair conformation form of trans 1 -tert-butyl -3-methylcyclohexane? a)Axial tert-butyl, equatorial methyl b)Axial tert-butyl,equatorial methyl c)equatorial tert-butyl, equatorial methyl d)equatorial tert-butyl, Axial methyl
A1. Draw the most stable conformations for: a)1-methyl-1-propylcyclohexane b)Trans-1-methyl-2-propylcyclohexane c)Cis-1-methyl-2-propylcyclohexane
Use your answers from Problem 2.48 to complete the table showing correlations between cis,trans and axial,equatorial for disubstituted derivatives of cyclohexane. Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3-dimethylcyclohexane, 1,4-dimethylcyclohexane. (a) Indicate by a label whether each methyl group is axial or equatorial.
A 1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group axial and one group equatorial. Explain.