C2323SS3 - Chem 2323 Study Sheet#3 Topic Alkanes and...

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1 C C h h e e m m 2 2 3 3 2 2 3 3 Study Sheet #3 Topic : Alkanes and Cycloalkanes: Stereochemistry Reference : McMurry chpt.4 Stereochemistry can be simply defined as the srudy of the 3-Dimensional structure of molecules I. pages : 112-119 Analysis represented in terms of a potential energy diagram : a plot of energy vs. molecular motion (i) ethane has two energetically different conformations : eclipsed and staggered - the barrier to rotation is due to torsional strain - value of one C-H / C-H interaction = 1 kcal mol -1 - total barrier 2.9 kcal mol -1 (ii) propane also has two energetically different conformations - value of one C-CH 3 / C-H interaction = 1.4 kcal mol -1 - total barrier 3.4 kcal mol -1 (iii) butane has four energetically different conformations : least stable eclipsed, gauche, eclipsed and anti - value of one CH 3 / CH 3 gauche interaction = 0.9 kcal mol -1 value of one CH 3 / CH 3 steric interaction = 2.5 kcal mol -1 - max. barrier 4.5 kcal mol
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C2323SS3 - Chem 2323 Study Sheet#3 Topic Alkanes and...

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