Chirality and Handedness

Presentation by Nourelle M.
Calam
Chirality:
Handedness
in Molecules
A presentation in Biochemistry
01
Presentation by Nourelle M. Calam
Define the property of chirality in
Learning molecules
Comprehend what the property of
handedness is all about
Focus Define Stereoisomerism

Learn how to designate handedness using
Fischer Projection Formulas
02 Discussion Points
Take a look at your

two hands
Are they the same? Or are they
different?
When you lay them on each other,
do they match one another?
Can they be superimposed?
03
No matter how much you try to position

and rotate your two hands, they can never
be superimposed upon each other. They
are after all, two different hands. You
cannot fit your left hand in a right-hand
glove, can you? Or if you happen to cut off
your left hand, it can never be replaced by
a right one and expect that you'll continue
to live as if everything's normal. There's
nothing normal with having two right
04 hands, right?
They may bear the same number of

fingers, with each set of fingers in one
hand being the same to that of the other.
And though they mirror one another, they
are, all in all, two different hands.

05

In nature, this property of handedness is also observed among many

types of molecules, including carbohydrates. These molecules may
seem similar, but they are different.
06
An important property of molecules,

including carbohydrates, is the
What is property of "HANDEDNESS".
Handedness?
Molecules that possess handedness

exist in two forms: a left-handed form
and a right-handed form.
07
For example, the common monosaccharide glucose
exists in two forms, one left-handed and the other
right-handed (how to determine the difference
between the two versions will be discussed on the
next slides)
What is
Handedness?
08
In one glance, they may seem like similar molecules.
But upon closer look, you can see that the two can
never be superimposed upon each other. Although
they literally have the same number and type of
components, the arrangement (configuration) of
these components in space vary among the two
glucose molecules?
What is
Handedness?
09
Does this
make the two
different
from one
another? Or
are they just
the same?
10
Non-superimposable mirror
molecules are said to be CHIRAL
molecules, while those that can be
superimposed are said to be
ACHIRAL molecules. Take a look at
the image on the right.
11
Chirality
In chemistry, what determines whether or not a
molecule possesses handedness? What
determines whether or not a molecule is chiral
or not?
To help you find the answer to these questions,

familiarize yourself with the element on the
right. They will be the star of the show moving
forward.
12
What you have to

remember
For organic and bioorganic compounds, the structural requirement for handedness (chirality) is
the presence of a carbon atom that has four (4) different groups bonded to it in a tetrahedral
orientation. This carbon atom is then referred to as the Chiral Center. There can be more than
one chiral centers in a compound, as long as the condition for determining chiral centers are
met. Furthermore, compounds having one or more chiral centers are said to be chiral.
Let's take a look at some examples.
13
Bromochloroiodomethane
Bromochloroiodomethane is the simplest example of a
chiral organic molecule. Being such, this molecule
exist in two forms. Because of its simple structure, it
is often considered to be the prototypical chiral
compound.
14
Does this satisfy the

condition for a molecule
to be considered chiral?
15
Does this satisfy the

condition for a molecule
to be considered chiral?
Note the four different groups

attached to the carbon atom: -H, -
BR, -CL, and -I. Thus, indeed, this
molecule is chiral.
16
The four different groups bonded

to a chiral center need not be just
single atoms as was the case in the
previous example. In the chiral-
center-containing molecule on the
right, the glyceraldehyde, 3 of the
4 groups are polyatomic entities.
17
The 4 different groups

attached to the carbon atom
at the chiral center in this
molecule are -H, -OH, -CHO,
and -CH2OH.
18
Let's take another

molecule, the
isopropyl alcohol, in
consideration.
19
Isopropyl Alcohol
Isopropyl alcohol is a 3-carbon

compound. Let us see if any of
the 3 carbon atoms in
isopropyl alcohol is a chiral
center.
20
Isopropyl Alcohol
21
Chiral centers within molecules are often denoted by a small

asterisk. Note the chiral centers in the following molecules.
Why aren't the other carbon atoms not denoted by an asterisk
not considered chiral centers?
22
1. A carbon atom involved in a multiple bond (double or triple

bond) cannot be a chiral center since it has a fewer than four
Guidelines groups bonded to it. To have four groups present, all bonds
about the chiral center must be single bonds.
for 2. The commonly encountered entities -CH3 and -CH2 in a

structural formula never involve chiral centers because of the
presence of two or more like hydrogen atoms.
identifying 3. Carbon atoms in a ring system, if not involved in multiple
bonding, can be chiral centers. Such carbon atoms have four
chiral bonds- two to neighboring atoms in the ring and two to
substituents on the ring. Chirality occurs when both (1) the two
centers substituents are different and (2) the two halves of the ring
emanating from the chiral centers are different. Please refer to
the following slide for an illustration of this concept.
23
Helpful note:
If the two substituents attached to the carbon atom in
observation, and the two halves of the rings are different, then
24 that carbon atom is chiral.
Let's have
some more
examples on
this
25
Indicate whether
the circled carbon
atom in each of the
following molecules
is a chiral center:
26
27
Solution:
This is a chiral center. The 4 different groups
attached to the carbon atom are -CH3, -Cl, -CH2-CH3,
and -H.
28
29
Solution:
No chiral center is present The carbon atom is attachd to only 3 groups
because it is involved in a double bond.
30
31
Solution:
No chiral center is present. Two or more groups attached to the carbon
atom are identical.
32
33
Solution:
The chirality rules for ring
carbon atoms are the same as
those for acyclic carbon atoms.
A chiral center is present. Two
of the groups are -H and -Br.
The third group, obtained by
proceeding clockwise around
the ring, is -CH2-CH2-Ch2. The
fourth group, obtained by
proceeding counterclockwise
around the ring, is -CH2-CHBr-
Ch2.
34
Presentation by Really Great Team
Organic molecules may contain more than one chiral center. For
example, the following compound has two chiral centers. The
four different groups attached to each of the chiral carbons are
shaded for easier identification.
35

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Presentation by Nourelle M.

Define the property of chirality in

Focus Define Stereoisomerism

Take a look at your

No matter how much you try to position

They may bear the same number of

Presentation by Nourelle M. Calam

In nature, this property of handedness is also observed among many

An important property of molecules,

Molecules that possess handedness

To help you find the answer to these questions,

What you have to

Let's take a look at some examples.

Does this satisfy the

Does this satisfy the

Note the four different groups

The four different groups bonded

The 4 different groups

Let's take another

Isopropyl alcohol is a 3-carbon

Chiral centers within molecules are often denoted by a small

1. A carbon atom involved in a multiple bond (double or triple

for 2. The commonly encountered entities -CH3 and -CH2 in a

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