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Interconversion of Fischer and zig-zag projections learning stereochemistry

with the help of hands

Article  in  Resonance · April 2010

DOI: 10.1007/s12045-010-0029-1

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 CLASSROOM

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
Email:
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.

IUPAC has defined a zig-zag projection as “a stereochemical Keywords

projection for an acyclic molecule (or portion of a molecule) Stereochemistry, conforma-
tional analysis, hands-on learn-
where the main chain is represented by a zig-zag line in the plane
ing, Fischer projections, zig-zag
and the substituents are shown above or below the plane” [2]. projection, C–C bond rotations.
Other, less correct names, such as skeletal structure and flying
wedge formula are also common for the same projection.

The conversion of Fischer into zig-zag projections has been

reported previously [1]. However, when it comes to visualization, 1
A common misconception
students will find the model described here easier to understand1. about the conversion of a Fischer
to zig-zag projection is that the
The method follows as below.
placement of two adjacent
groups (on the same side of the
Consider the Fischer projection (1) (Scheme 1).
Fischer projection) to the oppo-
site sides of the zig-zag back-
bone can provide the correct
zig-zag structure. This is true
only if we are concerned with the
relative stereochemistry. The
author’s method is suitable for
the correct representation of
absolute stereochemistry as
well.

Scheme 1.

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1. On paper, write the Fischer projection with thick and dashed

wedged bonds (2). In any Fischer projection, groups that are
attached with horizontal bonds are above the plane of the
paper. They are represented in 2 by a thick wedged line.
Those below the plane of paper are shown by a dashed
wedged line.

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.

3. Turn hands so that the fingers are pointing towards the

ceiling as shown in 4. The arrow between the hands indicates
the line of vision. Find the top and the bottom groups of
Fischer projections.

4. Order these terminal groups according to the position of

hands. The index finger will indicate the presence of the
particular group attached to a thick wedged line (4  5).

5. Join the terminal groups with the correct number of C atoms

in the eclipsed conformation (5  6).

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).

7. Rotate the appropriate C–C bonds to arrive at the zig-zag

projection (8).

Multiple C–C bond rotations that are mentioned in point 7 can be

challenging for students to perform. However, this can be easily
done if one knows that the conversion from eclipsed to zig-zag

352 RESONANCE  April 2010

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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

projection requires the rotation of the alternate C–C bonds. One

only has to know whether the first bond in the zig-zag skeleton is
rotated or not (Scheme 2). To spot the first rotated C–C bond, one
can use the method outlined below.

Draw a quadrant at any one of the terminal stereocenters in the

eclipsed projection 7, such that both the planar bonds are in the
same axis: +y or –y. For the selected stereocenter in 7, they are in
–y axis (Scheme 2). Now draw the same on the zig-zag skeleton
with terminal groups placed (9). If the planar group(s) has changed
its position from –y to +y axis or vice versa, then the bond has
been rotated. If there is no change then the bond has not been
rotated, and the following C–C bond has been rotated. The
rotated and non-rotated bonds alternate throughout the zig-zag
structure. Change dashed wedged bonds to thick wedged bonds
and vice versa on all the affected stereocenters as indicated. This
produces the zig-zag form 8.

Students may have difficulty in drawing the eclipsed skeleton. An

analogy is helpful. All rings drawn in planar form are in eclipsed
conformation. So, they can be used to draw the open chain
eclipsed conformations by erasing the correct number of carbons
from the cyclic planar structures. An example follows

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Scheme 3.

(Scheme 3). The conversion of Fischer projections into zig-zag

projections can be used in reverse to convert zig-zag projections
into Fischer projections.

On paper, the method may seem long (seven steps). However,

when performed, it takes only a few minutes. An important aspect
of the method is that it requires and teaches C–C bond rotation on
a 2D-surface (paper). It is essential for organic chemistry students
to be able to rotate a C–C bond on paper. Since the method
requires it, this reinforces and/or teaches the concept as well.

Acknowledgements

The author is grateful to Anne Herbert for the drawing of hands,

Susan Herbert for the reviewing of the manuscript and Samuel
Asem for performing the procedure by following the directions
mentioned in the paper.

References and Notes

[1] E Siloac, Bird-in-the-Hand method for dertermination of absolute con

figuration in Fischer projections, J. Chem. Educ., Vol.76, pp.798–799 and
references therein, 1999.
[2] G P Moss, Basic terminology of stereochemistry, Pure & Appl. Chem.
Vol.68, pp.2193–2222, 1996.

354 RESONANCE  April 2010

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