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Lecture 3 - interactions R equatorial R group R axial R...

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H H CH 3 H CH 3 H H H H 3 C H H CH 3 H CH 3 H H H CH 3 H 3 C H H H CH 3 H H CH 3 H H CH 3 H CH 3 H H H H CH 3 60 o 60 o 60 o 60 o 60 o 60 o looking at this bond of butane A B C D E F E rel (kcal/mol) 4.8 3.8 0.9
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pull this carbon down pull this carbon up A B C D E E rel (kcal/mol) 12.1 6.8 0 A B C D E Ring Flip of Cyclohexane
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E The larger the group attached to the cyclohexane, the more it wants to be situated in an equatorial position on the ring to minimize 1,3-diaxial/gauche
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Unformatted text preview: interactions. R equatorial R group R axial R group A Ratio E:A R = H 1:1 R = CH 3 18:1 R = CH 2 CH 3 21:1 R = CH(CH 3 ) 2 35:1 R = C(CH 3 ) 3 4800:1 R = F 1.5:1 R = F 2.4:1 R = Br 2.2:1 R = I 2.2:1 R = OH 4.5:1...
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