Drawing Stereochemical Structures

Newman Projections, Fischer Projections and Sawhorse Structures

1. How do we determine absolute configuration from a Newman projection?

Consider 2-bromo-3-methylpentane, a molecule with two chiral centers.

CH3 rotate H3C

H CH3 flatten the H CH3
H projection
CH3 CH3 sawhorse to (S,S)
slightly to
give a give a 3-D H Et
H Br Et Br
sawhorse structure ...
Et H Br ... add wedges
projection...
and dashes
The IUPAC name for this isomer is (2S, 3S)-2-bromo-3-methylpentane.
There are 3 more stereoisomers; what if you were also given this one?
CH3 Front carbon is inverted from the
H CH3 1st Newman structure, back
carbon is the same; must be (R, S)
Br H
Et
This stereoisomer is (2R, 3S)-2-bromo-3-methylpentane.

2. How do we convert a 3-D structure into a Fischer projection?

Using the (2S, 3S)-isomer from above, since we already know the stereochemical assignments,

Draw the CH3 CH3 CH3

CH3 Add the Assign
pentane C-2 is (R). H Br
Br H H Br C-3 to
other 2 Switch H and CH3 H
backbone give (S)
groups to Br to give (S).
vertically. Et Et Et Et
C-2
Remember, with Fischer drawings, if H is Horizontal, the assignment is Horribly wrong. This is because horizontal bonds
are understood to be coming out of the page in a Fischer drawing, so when we assign priorities to the 4 groups, the actual
configuration is opposite since H (lowest priority) is not directed into the page.

3. How do we convert a Fischer drawing into a Newman projection?

Using the (2S, 3S)-isomer once again:

Remember, Fischer Rotate

CH3 Tilt Fischer CH3 Et CH3
drawing is eclipsed. CH3 H CH3 sawhorse
H Br drawing to H CH3
Rotate around C2-C3 until C2
produce a
CH3 H CH3 H bond to get staggered and C3 are
sawhorse H Br
Et H Br conformation H Br Et eclipsed
projection Et