CHEM 109A Lecture #7

CHEM 109A Lecture #7 - CHEM 109A Lecture #7 CHAPTER 2...

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CHEM 109A Lecture #7 CHAPTER 2 Conformers of Monosubstituted Cyclohexanes The two chair conformers of a monosubstituted cyclohexane are not equivalent. The chair conformer in an equatorial position is more stable. 1,3-diaxial interaction – the interacting hydrogen or substituents are in 1,3- positions relative to each other, and it is an unfavorable steric interaction. Gauche conformer is 0.87 kcal/mol The substituent with the greater bulk near the 1,3-diaxial hydrogen will have greater preference in the equatorial position. To determine when a substituent is in the equatorial position you can use the following equaton: k eq = [equatorial conformer]/[axial conformer] and %=[equatorial conformer]/( [equatorial conformer] [axial conformer] ) * 100 The higher the : value the more equilateral it is Conformers of Disubstituted Cyclohexanes Cis isomer – both methyl substituents are on the same side of the cyclohexane ring Trans Isomer – the two methyl substituents are on opposite sides of the ring
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CHEM 109A Lecture #7 - CHEM 109A Lecture #7 CHAPTER 2...

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