The Fischer projection, devised by Hermann Emil Fischer

Hermann Emil Fischer

Hermann Emil Fischer, Emil Fischer was a German chemist and 1902 recipient of the Nobel Prize in Chemistry. He discovered the Fischer esterification. He developed the Fischer projection, a symbolic way of drawing asymmetric carbon atoms.-Early years:Fischer was born in Euskirchen, near Cologne,...

 in 1891, is a two-dimensional representation of a three-dimensional

Three-dimensional space

Three-dimensional space is a geometric 3-parameters model of the physical universe in which we live. These three dimensions are commonly called length, width, and depth , although any three directions can be chosen, provided that they do not lie in the same plane.In physics and mathematics, a...

 organic molecule by projection

Projection

Projection, projector, or projective may refer to:* The display of an image by devices such as:** Movie projector** Video projector** Overhead projector** Slide projector** Camera obscura** Projection screen...

. Fischer projections were originally proposed for the depiction of carbohydrates and used by chemist

Chemist

A chemist is a scientist trained in the study of chemistry. Chemists study the composition of matter and its properties such as density and acidity. Chemists carefully describe the properties they study in terms of quantities, with detail on the level of molecules and their component atoms...

s, particularly in organic chemistry

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

 and biochemistry

Biochemistry

Biochemistry, sometimes called biological chemistry, is the study of chemical processes in living organisms, including, but not limited to, living matter. Biochemistry governs all living organisms and living processes...

. The use of Fischer projections in non-carbohydrates is discouraged, as such drawings are ambiguous when confused with other types of drawing.

Conventions

All bond

Chemical bond

A chemical bond is an attraction between atoms that allows the formation of chemical substances that contain two or more atoms. The bond is caused by the electromagnetic force attraction between opposite charges, either between electrons and nuclei, or as the result of a dipole attraction...

s are depicted as horizontal or vertical lines. The carbon chain is depicted vertically, with carbon

Carbon

Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 atoms represented by the center of crossing lines. The orientation of the carbon chain is so that the C1 carbon is at the top. In an aldose

Aldose

An aldose is a monosaccharide that contains only one aldehyde group per molecule. The chemical formula takes the form Cnn. The simplest possible aldose is the diose glycolaldehyde, which only contains two carbon atoms....

, the carbon of the aldehyde

Aldehyde

An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....

 group is C1; in a ketose

Ketose

A ketose is a sugar containing one ketone group per molecule.With 3 carbon atoms, dihydroxyacetone is the simplest of all ketoses and is the only one having no optical activity. Ketoses can isomerize into an aldose when the carbonyl group is located at the end of the molecule...

 the carbon of the ketone

Ketone

In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

 group has the lowest possible number (usually C2).
A Fisher projection is used to differentiate between L- and D- molecules. On a Fischer projection, the penultimate carbon of D sugars are depicted with hydrogen

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

 on the left and hydroxide

Hydroxide

Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and a hydrogen atom held together by a covalent bond, and carrying a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, as a ligand, a nucleophile, and a...

 on the right. L sugars will be shown with the hydrogen on the right and the hydroxide on the left.

In a Fischer projection, all horizontal bonds project toward the viewer, while vertical bonds project away from the viewer. Therefore, a Fischer projection cannot be rotated by 90° or 270° in the plane of the page or the screen, as the orientation of bonds relative to one another can change, converting a molecule to its enantiomer

Enantiomer

In chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...

.
According to IUPAC rules all hydrogen atoms should preferably be drawn explicitly. Especially the hydrogen atoms of the end group of carbohydrates should be present.

Usage

Fischer projections are most commonly used in biochemistry and organic chemistry to represent monosaccharide

Monosaccharide

Monosaccharides are the most basic units of biologically important carbohydrates. They are the simplest form of sugar and are usually colorless, water-soluble, crystalline solids. Some monosaccharides have a sweet taste. Examples of monosaccharides include glucose , fructose , galactose, xylose...

s, but can also be used for amino acids or for other organic molecules. Since Fischer projections depict the stereochemistry

Stereochemistry

Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms within molecules. An important branch of stereochemistry is the study of chiral molecules....

 (three-dimensional structure) of a molecule

Molecule

A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...

, they are very useful for differentiating between enantiomers of chiral

Chirality (chemistry)

A chiral molecule is a type of molecule that lacks an internal plane of symmetry and thus has a non-superimposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom....

 molecules.

Other systems

Haworth projection

Haworth projection

A Haworth projection is a common way of representing the cyclic structure of monosaccharides with a simple three-dimensional perspective.The Haworth projection was named after the English chemist Sir Norman Haworth....

s are a related chemical notation used to represent sugars in ring form. The groups on the right hand side of a Fischer projection are equivalent to those below the plane of the ring in Haworth projections. Fischer projections should not be confused with Lewis structure

Lewis structure

Lewis structures are diagrams that show the bonding between atoms of a molecule and the lone pairs of electrons that may exist in the molecule. A Lewis structure can be drawn for any covalently bonded molecule, as well as coordination compounds...

s, which do not contain any information about three dimensional geometry

Molecular geometry

Molecular geometry or molecular structure is the three-dimensional arrangement of the atoms that constitute a molecule. It determines several properties of a substance including its reactivity, polarity, phase of matter, color, magnetism, and biological activity.- Molecular geometry determination...

.

See also

• Cahn-Ingold-Prelog priority rule
  Cahn-Ingold-Prelog priority rule
  The Cahn–Ingold–Prelog priority rules, CIP system or CIP conventions are a set of rules used in organic chemistry to name the stereoisomers of a molecule. A molecule may contain any number of stereocenters and any number of double bonds, and each gives rise to two possible configurations...
  
  
• Chair conformation
• Newman projection
  Newman projection
  A Newman projection, useful in alkane stereochemistry, visualizes chemical conformations of a carbon-carbon chemical bond from front to back, with the front carbon represented by a dot and the back carbon as a circle . The front carbon atom is called proximal, while the back atom is called distal...
  
  
• Natta projection
  Natta projection
  The Natta projection is a way to depict molecules with complete stereochemistry in two dimensions in a skeletal formula. This concept is named after Giulio Natta...