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Newman Projection Notes

The document provides instructions for drawing the Newman projection and perspective structure of 2,3-dimethylpentane. It begins with numbering the carbons and identifying the C2-C3 bond to look down. It then draws the Newman projection and identifies the lowest energy conformation with only two gauche interactions after rotating the front carbon. Finally, it draws the perspective structure from the Newman projection by adding substituents in the proper perspective.

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Alessandra De Silva
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290 views

Newman Projection Notes

The document provides instructions for drawing the Newman projection and perspective structure of 2,3-dimethylpentane. It begins with numbering the carbons and identifying the C2-C3 bond to look down. It then draws the Newman projection and identifies the lowest energy conformation with only two gauche interactions after rotating the front carbon. Finally, it draws the perspective structure from the Newman projection by adding substituents in the proper perspective.

Uploaded by

Alessandra De Silva
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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Castellano

From perspective drawing to Newman projection:

H3C H
Draw a Newman projection for the lowest energy conformer of
this molecule looking down the C2-C3 bond.
H3C H

First step, which atom is C2? Identify and number the atoms in the main chain as we did in
class, then look down the appropriate bond:

H3C H
4 I started numbering at the carbon closest
3
5 2 to the first branch. What's the IUPAC
1 name for this alkane?
H3C H
Draw a correct Newman projection. It may or may not represent the lowest energy conformer as
you first draw it . . . It is a good idea to draw a Newman that is in the staggered conformation
from the get-go . . . eclipsed, as you know, is generally high energy.

4 5
4 5
gauche CH2CH3
There are three 120° CCW
CH2CH3
gauche
H3C 3 H unfavorable gauche (front carbon) H 3 CH3
gauche 2 interactions in this
conformation . . . is there a 2
H3C H lower energy one? I'll H3C H
gauche CH3 rotate the front carbon 120
degrees counterclockwise.
gauche CH3
1
1

The conformation on the right only suffers two gauche interactions between large groups while
the one on the left suffers three. The conformation on the right is lower in energy (by about 0.9
kcal mol-1, the value of one CH3–CH3 gauche interaction).
Castellano

From Newman projection to perspective drawing:


CH3
H3C CH2CH3 Sketch a perspective diagram of the molecule in its lowest
energy conformation using the Newman projection that is
H3C H given as a starting point.
H
Rotate about the carbon single bond to get to the lowest energy conformer. The one above
suffers three unfavorable gauche interactions.

CH3
H CH3
I got here by rotating the front carbon clockwise by 120
degrees. Only two gauche interactions are observed now.
H3C H
CH2CH3
Next, identify the main chain (longest continuous chain).
1
CH3
H 2 CH3 Highlighted blue is the longest chain that is composed
3 of 5 continuous carbon atoms. Number the carbon
atoms in the chain according to IUPAC rules. I chose
H3C H carbon one as such since it is closest to the first
CH2CH3 branch! (a methyl group on carbon 2)
4 5
Draw the main chain in line angle form with a chain length of 5 carbons:

3
1 5
2 4

This last part is tricky and takes some practice. Identify (either on paper or in your mind's
eye) your frame of reference. I've indicated it above with the "eye". You're looking down
the C3-C2 bond in the Newman projection. Now add the substituents (2-methyl and 3-
methyl) in their proper perspective using dashes and wedges.

H CH3
2,3-dimethylpentane
H3C H
There are many ways to get to a correct answer. Find what works best for you through practice.

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