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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.

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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**Table 3.2: Energy Differences (\(\Delta G^\circ\)) for Equilibration of Monosubstituted Cyclohexanes, \(C_6H_{11}X\)** This table presents the energy differences (\(\Delta G^\circ\)) between equatorial and axial positions of various substituents on a cyclohexane ring, expressed in kcal/mol. | Substituent, X | \(\Delta G^\circ\) (equatorial - axial) (kcal/mol) | |---------------|-------------------------------------------------| | –H | 0.0 | | –F | -0.2 | | –CN | -0.2 | | –Cl | -0.5 | | –Br | -0.5 | | –C≡CH | -0.5 | | –OCH₃ | -0.6 | | –OH | -1.0 | | –COOH | -1.4 | | –CH₃ | -1.7 | | –CH=CH₂ | -1.7 | | –CH₂CH₃ | -1.8 | | –CH(CH₃)₂ | -2.1 | | –C₆H₅ | -2.9 | | –C(CH₃)₃ | -5.4 | **Graph Explanation:** On the right side of the table is a diagram showing energy changes during conformational transformations of the cyclohexane ring. - The graph depicts the potential energy as a function of cyclohexane conformation. - The y-axis represents energy, and the x-axis represents the conformational path. - The red curve shows energy peaks for less stable conformations such as half-chair, boat, and twist-boat. - The most stable conformation has the substituent \(X\) in the equatorial position, while the less stable has \(X\) in the axial position. - \(\Delta G^\circ\) is marked between these two states, indicating the energy difference.
Transcribed Image Text:**Table 3.2: Energy Differences (\(\Delta G^\circ\)) for Equilibration of Monosubstituted Cyclohexanes, \(C_6H_{11}X\)** This table presents the energy differences (\(\Delta G^\circ\)) between equatorial and axial positions of various substituents on a cyclohexane ring, expressed in kcal/mol. | Substituent, X | \(\Delta G^\circ\) (equatorial - axial) (kcal/mol) | |---------------|-------------------------------------------------| | –H | 0.0 | | –F | -0.2 | | –CN | -0.2 | | –Cl | -0.5 | | –Br | -0.5 | | –C≡CH | -0.5 | | –OCH₃ | -0.6 | | –OH | -1.0 | | –COOH | -1.4 | | –CH₃ | -1.7 | | –CH=CH₂ | -1.7 | | –CH₂CH₃ | -1.8 | | –CH(CH₃)₂ | -2.1 | | –C₆H₅ | -2.9 | | –C(CH₃)₃ | -5.4 | **Graph Explanation:** On the right side of the table is a diagram showing energy changes during conformational transformations of the cyclohexane ring. - The graph depicts the potential energy as a function of cyclohexane conformation. - The y-axis represents energy, and the x-axis represents the conformational path. - The red curve shows energy peaks for less stable conformations such as half-chair, boat, and twist-boat. - The most stable conformation has the substituent \(X\) in the equatorial position, while the less stable has \(X\) in the axial position. - \(\Delta G^\circ\) is marked between these two states, indicating the energy difference.
1. 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:1. 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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