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Concept
Fischer projection
Summary
In chemistry, the Fischer projection, devised by Emil Fischer in 1891, is a two-dimensional representation of a three-dimensional organic molecule by projection. Fischer projections were originally proposed for the depiction of carbohydrates and used by chemists, particularly in organic chemistry and biochemistry. The use of Fischer projections in non-carbohydrates is discouraged, as such drawings are ambiguous and easily confused with other types of drawing. The main purpose of Fischer projections is to show the chirality of a molecule and to distinguish between a pair of enantiomers. Some notable uses include drawing sugars and depicting isomers.
All bonds are depicted as horizontal or vertical lines. The carbon chain is depicted vertically, with carbon atoms sometimes not shown and represented by the center of crossing lines (see figure below). The orientation of the carbon chain is so that the first carbon (C1) is at the top. In an aldose, C1 is the carbon of the aldehyde group; in a ketose, C1 is the carbon closest to the ketone group, which is typically found at C2.
The proper way to view a Fischer projection is to vertically orient the molecule in relation to the carbon chain, have all horizontal bonds point toward the viewer, and orient all vertical bonds to point away from the viewer. Molecules with a simple tetrahedral geometry can be easily rotated in space so that this condition is met (see figures). Fischer projections are commonly constructed beginning with a sawhorse representation. To do so, all attachments to main chain carbons must be rotated such that resulting Newman projections show an eclipsed configuration. The carbon chain is then positioned vertically upward with all horizontal attachments pointing toward the viewer. Finally, attachments to main chain carbons that face away from the viewer are placed in the vertical position of the Fischer projection, and those that face toward the viewer are placed in the horizontal position of the Fischer projection.
Official source
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