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Fisher To Fly Wedge
Fisher To Fly Wedge
Fisher To Fly Wedge
Syed R Hussaini
Interconversion of Fischer and Zig-Zag Projections Department of Chemistry and
Learning Stereochemistry with the Help of Hands Biochemistry
The University of Tulsa
800 South Tuker Drive
Tulsa, OK 74104, USA.
Visualization of molecules in three dimensions is an important
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aspect of organic chemistry. The use of hands has been shown syed-hussaini@utulsa.edu
to be effective in the three-dimensional visualization of
molecules [1]. A method of looking at one’s own hands as a
model that allows students to see the interconversion of
Fischer and zig-zag projections is described in this article.
Scheme 1.
2. Make a victory sign ‘V’ with each of your hands and place
the left hand on top of the right hand. Position your hands so
that you are viewing your fingertips (refer to 3). Refer to 3
and note the arrows at the top of diagram saying, “view from
here”. The hands represent the terminal stereocenters. Your
fingers are the groups on thick wedged lines and the wrists
are the groups on dashed wedged lines. The hand on the top
is the top stereocenter in the Fischer projection. Identify the
group represented by any one of the fingers. In the present
case, the index finger of the top hand has been chosen.
6. Place the groups that are on the same side (left or right) in the
Fischer projection (1) to the same side (thick or dashed
wedged line) in the non Fischer projection (6 7).
Cl Scheme 2.
H F
+y I OH
CH3
Br
SH
CHO -y CH2OH
7
No rotation +y
CH2OH
OHC
Rotated
-y 9
Br F
I OH
CH 2OH
OHC
Cl CH 3
H SH
Scheme 3.
Acknowledgements