At room temperature, 1,2-dibromoethane exists as an equilibrium mixture in which 89% of

Chapter 3, Problem 31

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At room temperature, 1,2-dibromoethane exists as an equilibrium mixture in which 89% of themolecules are in an anti conformation and 11% are gauche. The comparable ratio for butaneunder the same circumstances is 72% anti and 28% gauche. Suggest an explanation for the difference,bearing in mind that Br is sterically smaller than CH3 (see 30). (Hint: Considerthe polarity of a CBr bond and consequent electrostatic effects.)

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