Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 3, Problem 33P
Interpretation Introduction

Interpretation:The greater percentage of anti-conformation in case of 1,2-dibromoethane relative to simple butane should be explained.

Concept introduction: Various interconvertible forms that result from rotation around the C–C bind in ethane are termed as conformer. To depict such conformation Newman projections are written. These are obtained by conversion of hashed-wedged line structure simply when molecule is viewed in a plane along the C–C as illustrated below:

  Organic Chemistry: Structure and Function, Chapter 3, Problem 33P , additional homework tip  1

Thus in Newman's projection of simple ethane molecule the “front” C is depicted as intersection of three bonds with three attached H . The other three bonds connect to the large circle corresponding to “back” carbon in C–C bond.The potential energy shows peaks and falls. This corresponds to transition from staggered and eclipsed conformation molecule adopts with each 60 ° rotation as illustrated in lateral view below.

  Organic Chemistry: Structure and Function, Chapter 3, Problem 33P , additional homework tip  2

Staggered conformation that has substituents on both carbons farthest apart is regarded most stable due to least torsional strain, whereas the eclipsed has large amount of torsional strain due to steric repulsions. Therefore in potential-energy diagram, peak corresponds to eclipsed while the valley corresponds to stable staggered conformation.

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A chemist synthesized compound X as a racemic mixture. When the ketone group in X was enzymatically reduced to the corresponding alcohol, a 100% yield was obtained of the product shown below. Choose the statement that best describes this result. ОН enzyme C;H1 `OCH,CH; pH 4.0 C3H1 `OCH,CH3 ОН ÕH X (racemic) (100% yield) One enantiomer of compound X reacts quickly with the enzyme. The other enantiomer of compound X is unreactive, but rapidly equilibrates with the reactive enantiomer under the reaction conditions. Since compound X was racemic, it makes sense that only a single product was obtained. O The product is a meso compound, so either enantiomer of compound X gives the same product. One enantiomer of compound X reacts quickly with the enzyme, while the other enantiomer of compound X remains unchanged.
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