Draw the conformation for methoxycyclohexane with the methoxy group axial and the conformation with the methoxy group equatorial, include all hydrogen atoms on cyclohexane and label each as axial or equatorial. Using the values from Table 3.2, which conformation is more stable and by how much energy? Calculate the Keq for the equilibrium between axial and equatorial cyclohexane at 298 K. Calculate the percentage of each conformation present at this temperature.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter2: Alkanes And Cycloalkanes
Section2.5: Conformations Of Alkanes And Cycloalkanes
Problem 2.9P: Following is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a)...
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Table 3.2
odi ensiminimi
CVEWLE
-F
Substituent, X
bx stl
-H lliw sadi sah asupsto
toutieng Isixs
-0.2
od 24swin modis -0.2
-0.5
-0.5
11
-CN
-CI
-Br
1015
Energy differences (AG) for equilibration of monosubstituted cl
cyclohexanes, C6H₁X
zadobadiam mord inprobib
a
abruogmos.sondy the 101-gur sel
-OCH3
-OH
-COOH
-CH3 CH#
-CH=CH₂
-CH₂CH3
-CH(CH3)2
AG (equatorial-axial) moc
(kcal mol-1)
-C6H5
-C(CH3)3
-C=CHDimethylcycloban-0.5
goils, bars in caf
H H
-0.6
-1.0
-1.4
-1.7
-1.7
-1.8 T
-2.1
-2.9
-5.4
Energy
vode
Joy wibor b
folavalvulad
(Less stable conformations:
half-chair, boat, twist-boat)
H
+
AGⓇ
314
H
-X
at E sugia
Transcribed Image Text:Table 3.2 odi ensiminimi CVEWLE -F Substituent, X bx stl -H lliw sadi sah asupsto toutieng Isixs -0.2 od 24swin modis -0.2 -0.5 -0.5 11 -CN -CI -Br 1015 Energy differences (AG) for equilibration of monosubstituted cl cyclohexanes, C6H₁X zadobadiam mord inprobib a abruogmos.sondy the 101-gur sel -OCH3 -OH -COOH -CH3 CH# -CH=CH₂ -CH₂CH3 -CH(CH3)2 AG (equatorial-axial) moc (kcal mol-1) -C6H5 -C(CH3)3 -C=CHDimethylcycloban-0.5 goils, bars in caf H H -0.6 -1.0 -1.4 -1.7 -1.7 -1.8 T -2.1 -2.9 -5.4 Energy vode Joy wibor b folavalvulad (Less stable conformations: half-chair, boat, twist-boat) H + AGⓇ 314 H -X at E sugia
Draw the conformation for methoxycyclohexane with the methoxy group axial and the
conformation with the methoxy group equatorial, include all hydrogen atoms on cyclohexane
and label each as axial or equatorial. Using the values from Table 3.2, which conformation is
more stable and by how much energy? Calculate the Keq for the equilibrium between axial
and equatorial cyclohexane at 298 K. Calculate the percentage of each conformation present
at this temperature.
Transcribed Image Text:Draw the conformation for methoxycyclohexane with the methoxy group axial and the conformation with the methoxy group equatorial, include all hydrogen atoms on cyclohexane and label each as axial or equatorial. Using the values from Table 3.2, which conformation is more stable and by how much energy? Calculate the Keq for the equilibrium between axial and equatorial cyclohexane at 298 K. Calculate the percentage of each conformation present at this temperature.
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