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Chapter 11: Problem 18

Draw Newman projections of four different conformations of butane. Rank them in stability.

Short Answer

Expert verified
The most stable conformation of butane is anti, and the least stable is eclipsed (0°).

Step by step solution

01

Draw the Newman Projections

Newman Projections are drawn by looking directly along a chosen bond. When drawing the projections of butane, focus on the 2-3 bond. Draw a dot for the front carbon and a circle for the back carbon. The hydrogens attached to each carbon are shown using lines. Butane has 4 different conformations: eclipsed (0°), gauche (60°), eclipsed (120°) and anti (180°). Draw these four Newman Projections.
02

Analyze Torsional Strain

Torsional strain is caused by the repulsion between electrons in the bonds. In an eclipsed conformation, the hydrogen atoms in the front and back carbon are directly aligned which increases the torsional strain making it less stable. In a staggered conformation as in gauche and anti forms, the hydrogens are not directly aligned which decreases the torsional strain making it more stable.
03

Rank the Conformations

According to the torsional strain, the anti conformation is the most stable because the hydrogens are as far apart as possible, then comes the gauche conformation as the hydrogens atoms are slightly closer, followed by the eclipsed conformation (120°) and the least stable is the eclipsed conformation (0°) due to maximum torsional strain.

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