Substituents are to be added to the incomplete Newman projections to represent the first molecule after +60° and +120° rotations of the back carbon. Concept introduction: Newman projection is a 2-D depiction of a molecule observed down the bond of attention. In this projection, carbon atoms directly attached by the bond of attention shown explicitly. The front carbon shown as a point and back side carbon atom shown as a circle. The back-carbon atom connected to the circle and front carbon atom converge at the point. The bond of interest is not visible; instead, it must be imagined as connecting the front and back carbons. A Newman projection does, however, highlight the other bonds to the front and back atoms.

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Chapter 4, Problem 4.3YT

Interpretation Introduction

Interpretation:

Substituents are to be added to the incomplete Newman projections to represent the first molecule after +60° and +120° rotations of the back carbon.

Concept introduction:

Newman projection is a 2-D depiction of a molecule observed down the bond of attention. In this projection, carbon atoms directly attached by the bond of attention shown explicitly. The front carbon shown as a point and back side carbon atom shown as a circle. The back-carbon atom connected to the circle and front carbon atom converge at the point. The bond of interest is not visible; instead, it must be imagined as connecting the front and back carbons. A Newman projection does, however, highlight the other bonds to the front and back atoms.

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9. Draw the Newman projection for each of the following molecules, looking down the bond indicated with an arrow. Do not rotate the molecule. H H Br H CH3 "H HO H CH3 HH CH3 OCH₂CH3 HAH (H3C)3CH CH3 10. Draw the corresponding dash-wedge structure for each of the following single bond Newman projections. H H H HO H -CH₂CH3 H CH₂CH₂CH3 Br H CH3 ''C(CH3)3 H H3C CH3 H3C CH3 H Br H3C- CH H3C H H

For the the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. 2,3-dimethylpentane ECLIPSING Interactions AB Energy kcal/mol H/H 1.0 H / Me 1.4 H/Et 1.5 H/i-Pr 1.6 H/t-Bu 3.0 Me / Me 2.6 Me / Et 2.7 Me/i-Pr 3.0 GAUCHE A. Interactions Me / Me Me / Et Me / i-Pr Me / t-Bu Et / Et Et / -Pr Et/t-Bu i-Pr/i-Pr B Energy kcal/mol 0.9 0.95 1.1 2.7 1.1 1.6 3.0 2.0

For the the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. Lowest Energy Conformation 3-D sawhorse Newman ECLIPSING Interactions AB H/H H/Me H / Et H/i-Pr Energy kcal/mol 1.0 1.4 1.5 1.6 H/ t-Bu 3.0 Me / Me 2.6 Me / Et 2.7 Mei-Pr 3.0 GAUCHE A. Interactions Me / Me Me / Et Me / i-Pr Me / t-Bu Et / Et Et/i-Pr Et / t-Bu i-Pr/i-Pr 3-D sawhorse Energy kcal/mol Newman 0.9 0.95 1.1 2.7 1.1 1.6 Highest Energy Conformation 3.0 2.0