Carbohydrates Chirality

CARBOHYDRATES
CHIRALITY
CHIRALITY
• Stereoisomers are isomers that differ in spatial arrangement of
atoms. One of the most interesting types of isomer is the
mirror-image stereoisomer, a non-superimposable set of two
molecules that are mirror images of one another.
• The existence of these molecules are determined by a concept
known as chirality. The word “chiral” was derived from the
Greek word for hand, because our hands are a good example of
chirality since they are non-superimposable mirror images of
each other.
Chirality
• Chiral molecules are molecules that are not identical to their mirror
images
• Chirality is exhibited by molecules that do not have a plane of
symmetry; a molecule that has a plane of symmetry in any of its
possible conformation is identical to its mirror image and is achiral.
• Usually, lack of plane of symmetry is exhibited by molecules
containing a carbon atom bonded to different atoms or group of
atoms, such an atom is called a chiral center or stereogenic center.
MONOSACCHARIDES
• CHIRALITY: HANDEDNESS IN MOLECULES
• Most common monosaccharides exist in two forms:
• A left handed form and right handed forms (Mirror
images)
• 2 classes on the basis of mirror images
• Superimposable mirror image – are images that coincide
at all points when the images are laid upon each other.
• Nonsuperimposable mirror image – are image where not
MONOSACCHARIDES
Why is one chiral and the other not?
• The answer is that the flask has a plane
of symmetry and your hand does not.
• A plane of symmetry is a plane or a line
through an object which divides the
object into two halves that are mirror
images of each other.
• When looking at the flask, a line can be
drawn down the middle which separates it
into two mirror image halves.
• However, a similar line down the middle of
a hand separates it into two non-mirror
image halves.
• This idea can be used to predict chirality.
If an object or molecule has a plane of
symmetry it is achiral. If it lacks a plane
of symmetry it is chiral.
CHIRAL AND NONCHIRAL/ACHIRAL
Chiral Molecules
• The term chiral, from the Greek work for 'hand', refers to
anything which cannot be superimposed on its own mirror
image.
• Certain organic molecules are chiral meaning that they are not
superimposable on their mirror image.
• Chiral molecules contain one or more chiral centers, which
are almost always tetrahedral carbons with four different
substituents.
Chiral Molecules
• Consider the molecule A below: a tetrahedral carbon, with four different substituents denoted by
balls of four different colors. The mirror image of A, which we will call B, is drawn on the right side
of the figure, and an imaginary mirror is in the middle. Notice that every point on A lines up
through the mirror with the same point on B: in other words, if A looked in the mirror, it would see
B looking back.
Chiral Molecules
• Now, if we flip compound A over and try to superimpose it point for point on compound
B, we find that we cannot do it: if we superimpose any two colored balls, then the other
two are misaligned. A is not superimposable on its mirror image (B), thus by definition A
is a chiral molecule. It follows that B also is not superimposable on its mirror image (A),
and thus it is also a chiral molecule.
MONOSACCHARIDES
• CHIRAL and ACHIRAL
• A molecule that contains a chiral center is said to be chiral
A carbon atom bonded to different atoms or group of

atoms is called a chiral center.
An example is shown in the
bromochlorofluoromethane molecule shown
in part (a) of the figure below.
• This carbon, is attached to four different
substituents making it chiral. which is often
designated by an asterisk in structural
drawings.
• If the bromine atom is replaced by another
chlorine to make dichlorofluoromethane, as
shown in part (b) below, the molecule and its
mirror image can now be superimposed by
simple rotation.
• Thus the carbon is no longer a chiral center.
Upon comparison, bromochlorofluoromethane
lacks a plane of symmetry while
dichlorofluoromethane has a plane of
symmetry.
EXAMPLE
• Determining if a carbon is bonded to four distinctly different substituents can often be difficult to
ascertain. Remember even the slightest difference makes a substituent unique. Often these
difference can be distant from the chiral carbon itself. Careful consideration and often the building
of molecular models may be required. A good example is shown below. It may appear that the
molecule is achiral, however, when looking at the groups directly attached to the possible chiral
carbon, it is clear that they all different. The two alkyl groups differ by a single -CH2- group which is
enough to consider them different.
Learning check:
• CHIRALITY

Carbohydrates Chirality

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CARBOHYDRATES

A carbon atom bonded to different atoms or group of

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