Ch_322a_4.012

Ch_322a_4.012 - Conformational Features of Butane The...

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Conformational Features of Butane The Internal Bond in CH 3 CH 2 -CH 2 CH 3 Rotation around the internal bond in butane introduces conformational features different from the CH 3 -C X 3 systems. Structures of the general type X CH 2 -CH 2 X, where X is larger than H, have rotational barriers with significant steric strain in the eclipsed conformation where the X groups are aligned. These conformational features are more easily noted when the several extreme conformations (staggered and eclipsed) are analyzed as substituted ethanes. C C H H H CH 3 CH 3 H
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Analysis of the Extreme Conformations During one complete rotation around the internal bond in butane, the three staggered conformations include two called "gauche" and one called "anti." C C H H H CH 3 CH 3 H 120 o rotation C C H H H CH 3 CH 3 H 120 o rotation C C H H H CH 3 CH 3 H The Newman projection formulas as viewed from the left are: CH 3 H H H H CH 3 120 o rotation CH 3 H H H H CH 3 120 o rotation CH 3 H H H H CH 3 anti gauche gauche steric strain The staggered anti is more stable than the two equivalent staggered
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Ch_322a_4.012 - Conformational Features of Butane The...

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