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Chapter 26: Problem 44

Draw Newman projections for the staggered and eclipsed conformations of 2 -methylpentane for rotation about the \(\mathrm{C} 2-\mathrm{C} 3\) bond. Which conformation is lowest in energy?

Short Answer

Expert verified
The staggered conformation of 2-methylpentane on rotation about the C2-C3 bond is lowest in energy.

Step by step solution

01

Drawing Newman Projection for Staggered Conformation

Begin by identifying the C2-C3 bond. Draw a circle representing the front carbon atom (C2), and a point in the circle marking the back carbon atom (C3). Next, sketch three lines at a 120° angle to each other representing the hydrogen and methyl group bonded to the front carbon. Similarly, draw three lines from the back carbon, ensuring that each line aligns with the spaces between the lines from the front carbon (not on top of them). This gives the staggered conformation.
02

Drawing Newman Projection for Eclipsed Conformation

Similar to before, identify the C2-C3 bond and draw a circle representing the C2 atom and a point in the circle marking the C3 atom. Draw lines representing the hydrogen and methyl group bonded to the front carbon. However, in this case, draw the lines from the back carbon directly behind the front carbon's lines, giving the eclipsed conformation.
03

Determine Lowest Energy Conformation

Under normal conditions, the staggered conformation is lower in energy and thus more stable due to decreased steric strain. So, for 2-methylpentane on rotation about the C2-C3 bond, the staggered conformation is the lowest energy conformation.

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Most popular questions from this chapter

Draw and name all the isomers of (a) \(\mathrm{C}_{6} \mathrm{H}_{14}\) (b) \(\mathrm{C}_{4} \mathrm{H}_{8} ;\) (c) \(\mathrm{C}_{4} \mathrm{H}_{6}\). [Hint: Do not forget double bonds, rings, and combinations of these.].

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