One of the chair conformations of cis-1-bromo-3-methylcyclohexane is more stable than the other by 14.0 kJ/mol. Use this, and the table below, to estimate the energy cost of a 1,3-diaxial interaction between a bromine atom and a methyl group. Substituent kJ/mol Substituent kJ/mol 1,3-Diaxial Strain Energies for Monosubstituted Cyclohexanes -CN, cyano -F -I -C=CH, ethynyl 0.85 -CI -Br -OH 0.4 -C6H5 0.5 0.95 1.1 1.2 1.95 6.3 -NH₂ -COOH 2.95 -CH3 2.95 -CH=CH₂ 3.55 3.64 -CH₂CH3 -CH(CH3)2 4.5 -C(CH3)3 3.65 10.5 (Round your answer to one decimal place.) kJ/mol

One of the chair conformations of cis-1-bromo-3-methylcyclohexane is more stable than the other by 14.0 kJ/mol. Use this, and the table below, to estimate the energy cost of a 1,3-diaxial interaction between a bromine atom and a methyl group. Substituent kJ/mol Substituent kJ/mol 1,3-Diaxial Strain Energies for Monosubstituted Cyclohexanes -CN, cyano -F -I -C=CH, ethynyl 0.85 -CI -Br -OH 0.4 -C6H5 0.5 0.95 1.1 1.2 1.95 6.3 -NH₂ -COOH 2.95 -CH3 2.95 -CH=CH₂ 3.55 3.64 -CH₂CH3 -CH(CH3)2 4.5 -C(CH3)3 3.65 10.5 (Round your answer to one decimal place.) kJ/mol

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

Section: Chapter Questions

Problem 2.45P: Gibbs free energy differences between axial-substituted and equatorial-substituted chair...

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One of the chair conformations of cis-1-chloro-3-methylcyclohexane is more stable than the other by 15.5 kJ/mol. Use this, and the table below, to estimate the energy cost of a 1,3-diaxial interaction between a chlorine atom and a methyl group. 1,3-Diaxial Strain Energies for Monosubstituted Cyclohexanes kJ/mol Substituent Substituent kJ/mol -NH2 -CN, cyano 0.4 2.95 -F 0.5 -COOH 2.95 -C=CH, ethynyl 0.85 -CH=CH2 3.55 -CH3 -I 0.95 3.64 -CH2CH3 -Cl 3.65 1.1 -CH(CH3)2 1.2 4.5 -Br -C(CH3)3 10.5 -ОН 1.95 -CGH5 6.3 (Round your answer to one decimal place.) kJ/mol
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Calculate strain energy for the conformer pictured below, using strain energy increments from the table. Strain Energy for Alkanes Interaction / Compound kJ/mol kcal/mol H:H eclipsing 4.0 1.0 H: CH3 eclipsing 5.8 1.4 CH3 : CH3 eclipsing 11.0 2.6 gauche butane 3.8 0.9 cyclopropane 115 27.5 cyclobutane 110 26.3 cyclopentane 26.0 6.2 cycloheptane 26.2 6.3 cyclooctane 40.5 9.7 (Calculate your answer to the nearest 0.1 energy unit, and be sure to specify units, kJ/mol or kcal/mol. The answer is case sensitive.) CH3 H3CH,C CH3 H3C CH3 Previous Next