THE UNIVERSITY OF LAHORE,

SARGODHA CAMPUS
B.Sc. (Hons) Chemistry

SUBMITTED BY:

SHAHZAD KHAN

REG. NO. :

BSCSR07191003

SUBMITTED TO:

MAM RUBINA MUKHTAR

TOPIC:

Basic intro of Chiral compounds,

Enantiomers, Diastereomers

and Meso compounds

DATED:

5/10/2021

COURSE TITLE:

ORGANIC CHEMISTRY II

SEMESTER:

BS 5TH
Chirality:
In chemistry, a molecule or ion is called chiral if it cannot be superposed on its mirror image by any
combination of rotations and translations. This geometric property is called chirality. The terms are
derived from Ancient Greek meaning "hand"; which is the canonical example of an object with this
property.

A chiral molecule or ion exists in two stereoisomers that are mirror images of each other, called
enantiomers; they are often distinguished as either "right-handed" or "left-handed" by their absolute
configuration or some other criterion. The two enantiomers have the same chemical properties, except
when reacting with other chiral compounds. They also have the same physical properties, except that they
often have opposite optical activities. A homogeneous mixture of the two enantiomers in equal parts is
said to be racemic, and it usually differs chemically and physically from the pure enantiomers.

A chiral molecule or ion typically contains a chiral center or stereo center. When that center coincides
with an atom, the substance is said to have point chirality. In chiral organic compounds, a stereo center is
often an asymmetric carbon. Multiple stereo centers may give rise to additional stereoisomers. On the
other hand, a molecule with an even number of stereo centers may have one or more stereoisomers which
are not chiral.

Chirality is an important concept for stereochemistry and biochemistry. Most substances relevant to
biology are chiral, such as carbohydrates (sugars, starch, and cellulose), the amino acids that are the
building blocks of proteins, and the nucleic acids. In living organisms, one typically finds only one of the
two enantiomers of a chiral compound. For that reason, organisms that consume a chiral compound
usually can metabolize only one of its enantiomers. For the same reason, the two enantiomers of a chiral
pharmaceutical usually have vastly different potencies or effects.

Definition
Chirality is based on molecular symmetry. Specifically, a chiral compound can contain no improper axis
of rotation (Sn), which includes planes of symmetry and inversion center. Chiral molecules are always
dissymmetric (lacking Sn) but not always asymmetric (lacking all symmetry elements except the trivial
identity). Asymmetric molecules are always chiral

Molecular symmetry and chirality

 Rotational
Improper rotational elements (Sn)
axis (Cn)

Achiral Achiral
Chiral
mirror plane inversion centre
no Sn
S1 = σ S2 = i

C1

C2

Meso Compounds:
Meso compounds are achiral compounds that has multiple chiral centers. It is
superimposed on its mirror image and is optically inactive despite its stereocenters.

Introduction

In general, a meso compound should contain two or more identical substituted

stereocenters. Also, it has an internal symmetry plane that divides the compound in
half. These two halves reflect each other by the internal mirror. The
stereochemistry of stereocenters should "cancel out". What it means here is that
when we have an internal plane that splits the compound into two symmetrical
sides, the stereochemistry of both left and right side should be opposite to each
other, and therefore, result in optically inactive. Cyclic compounds may also be
meso.

Identification

If A is a meso compound, it should have two or more stereocenters, an internal

plane, and the stereochemistry should be R and S.

Look for an internal plane, or internal mirror, that lies in between the compound.

The stereochemistry (e.g. R or S) is very crucial in determining whether it is a

meso compound or not. As mentioned above, a meso compound is optically
inactive, so their stereochemistry should cancel out. For instance, R cancels S out
in a meso compound with two stereocenters.

Example

This molecule has a plane of symmetry (the horizontal plane going through the red broken line)
and, therefore, is achiral; However, it has two chiral carbons and is consequentially a meso
compound.

Example 2
This molecules has a plane of symmetry (the vertical plane going through the red broken line
perpendicular to the plane of the ring) and, therefore, is achiral, but has has two chiral centers.
Thus, its is a meso compound.

Diastereomers:

Diastereomers are stereoisomers that are not mirror images of one another and are non-superimposable on
one another. Stereoisomers with two or more stereocenters can be diastereomers. It is sometimes difficult
to determine whether or not two molecules are diastereomers. For introductory purposes, simple
molecules will be used as examples. More complex examples will be given later.

For example, consider the following molecules.

These molecules are not mirror images of one another. Additionally, these molecules are non-
superimposable because if one of these molecules is flipped 180 degrees (so that the alcohols and methyls
are aligned, as shown below), the stereochemistry is different at one carbon (the alcohols) and the same at
another carbon (the methyls). Therefore, these molecules are diastereomers.