What is organic chemistry?

Chemistry of Carbon
We used to describe organic chemistry as the
chemistry of living things.
Since the chemistry of living things is based on
carbon, the chemistry of carbon compounds has
come to be known as organic chemistry.
It now includes the study of carbon compounds
which are not found in living things and so is an
incredibly large branch of modern chemistry.
Im made of what???
Guess how many elements your
body is made up of?
25 elements make up all living
things
About 97% of your bodys mass is
made of just 4 elements: oxygen,
carbon, hydrogen, & nitrogen.
Two other major elements are
phosphorous & sulfur.
 Why is life based on the element carbon?

There are two important properties of carbon

that make it a suitable element to form the
compounds in living things:
Firstly, carbon atoms can link together to
form stable chains of great length.
Why is life based on the element carbon?

Carbon atoms bind strongly

to each other and form very
large molecule which are
built around this carbon
'backbone'.

The covalent bond between two carbon atoms is

strong so that the backbones are stable. In all of
these compounds simple sub-units called
monomers are linked together by condensation
reactions.
3 Types of Carbon Backbones
 Carbon forms long chains

One carbon chain may contain hundreds of carbon atoms.

Unlike other elements, carbon atoms can bond to each
other to form very long chains.
A very large carbon-based molecule made of repeating
units is called a polymer. Each unit of a polymer is called a
monomer.
Polymers can be thousands of atoms long
 Carbon forms Rings
When there are three or more carbons in a straight chain, the ends can be
joined to make rings.
Carbon-based molecules also can be shaped like rings. Most carbon rings
contain 5 or 6 carbon atoms.

One of the most important carbon rings is benzene.

It has 6 carbons & 6 hydrogens , with alternating double bonds.

They often have very strong smells or aromas, so they are called
aromatic compounds.
 What makes carbon so special?

It has a central role in all living organisms.

It has 4 valence electrons.
It makes 4 covalent bonds.
It can bond with any
element,
but really loves to bond with other carbon atoms and make
long chains
 Carbon forms four bonds
Carbon can form four bonds, and forms strong
covalent bonds with other elements
This can be represented in many ways

O Cl CH3 CH3
H Cl
C C CH C
H3C CH3
C C Cl C CH
H H CH CH3 CH3
CH

CH2 CH2 CH2 CH2 CH3

H3C CH2 CH2 CH2 CH2
 Silicon is similar to carbon. Why are there no
life forms based on silicon?

Silicon is unsuitable because, although it is a valence IV

element like carbon (4 electrons to share),
BUT the silicon-silicon covalent bond is not strong enough for it
to form long stable chains.
So, it can not form molecules of the complexity needed to make
up cells like carbon can!

Silicon is just like carbon, but:

Larger: five- and six-coordinate Si-C bond covalent, unreactive
structures positive Si-O, Si-F very ("abnormally") strong
More electropositive: easier attack Si-Cl, Si-Br, Si-I reactive
by nucleophiles Si-Si weak (!)
Does not want to form multiple Si=Si and Si=C weak, very reactive

Bonds- SiO2 vs CO2

 Hydrocarbons
Hydrocarbons are organic compounds that are made of only hydrogen
and carbon atoms. They are found in many places, including crude oil
and natural gas.
 Hydrocarbons
Alkanes C C Molecular formula Alkenes C C
H H H H H Shows atoms in the H H H
H C C C C C H
molecule
Structural formula H C C C C C H
H H H H H
Shows how they are H H H H H

C5H12 all connected C5H10

Alkynes C C Saturated: Aromatics

single bond H
H H H H C H
present C C
H C C C C C H Unsaturated: C C
H C H
H H H double or H
C5H8 triple bond C6H6
present
Alkanes
Naming Alkanes
 Alkanes
Alkanes, cannot be named based on their molecular formulas
For example, all of the molecules shown below share the
same molecular formula, C6H14
(hexacarbon tetradecahydride?)
H H H H H H
H C C C C C C H
H H H H H H

n-hexane
H H
H H H C H
H C H
H C H H C H
H H H H H H
H H H H H H H H H C C C C H
H C C C C H
H C C C C C H H C C C C C H H H H H H H
H H H H H H H H H H
H C H H C H

2-methyl-pentane 3-methyl-pentane H H

2,2-dimethylbutane 2,3-dimethylbutane
 Properties of Alkanes

Methane to butane are gases.

From pentane onwards, approximately the next
thirty alkanes in the series are liquids.
Alkanes with even longer chains are waxy solids.
They are typical covalent compounds, insoluble in
water but able to mix with each other.
Alkanes burn in oxygen to produce carbon dioxide
and steam.
 Cycloalkanes
When there are three or more carbons in a straight chain, the ends can be
joined to make rings.
In naming these molecules, the prefix cyclo- is used to indicate the ring:
Skeletal structural formulas are used to represent the rings in structural
formulas:

As Parent Chain As Substituent Group

C3H6
cyclopropane R cyclopropyl-

C4H8

cyclobutane R cyclobutyl-

C5H10

cyclopentane R cyclopentyl-

C6H12
R
cyclohexane cyclohexyl-
 The Nature of Organic Molecules
Organic chemistry is the study of carbon
compounds.
Carbon is tetravalent; it always forms four bonds.
Organic molecules have covalent bonds.
 The Nature of Organic Molecules

When carbon bonds to a more

electronegative element, polar
covalent bonds result.
Organic molecules have specific Chloromethane, CH3Cl
three-dimensional shapes.
In a tetrahedral molecular
geometry, a central atom is
located at the center with four
substituents that are located at
the corners of a tetrahedron.
The bond angles 109.5
 The Nature of Organic Molecules
Organic molecules often contain nitrogen and oxygen in addition
to carbon and hydrogen.
Nitrogen can form single, double, and triple bonds to carbon.
Oxygen can form single and double bonds.
Hydrogen can only form single bonds to carbon.
Covalent bonding
Lower melting and boiling points than inorganic salts
Many organic compounds are liquids or low melting solids at
room temperature, and a few are gases.
Most organic compounds are insoluble in water.
Only Polar organic molecules dissolve in water.
 Families of Organic Molecules:
Functional Groups
A functional group is an atom, group of atoms or bond
that gives a molecule a particular set of chemical and
physical properties
Organic compounds can be classified into families
according to structural features.
The chemical behavior of family members is often
predictable based on their specific grouping of atoms.
The chemistry of an organic molecule is primarily
determined by the functional groups it contains, not by
its size or complexity.
Lots of ways to draw this
Families of Organic Molecules: Functional Groups
The first four families are hydrocarbons, organic
compounds that contain only carbon and hydrogen.
Alkanes have only single bonds and contain no functional groups.

Alkenes contain a carboncarbon double-bond functional group.

Alkynes contain a carboncarbon triple-bond functional group.

Aromatic compounds contain a six-membered ring of carbon

atoms with three alternating double bonds.
The Structure of Organic Molecules: Alkanes and Their Isomers
The general rule for all hydrocarbons except methane is that each
carbon must be bonded to at least one other carbon.
The carbon atoms bond together to form the backbone of the
compound, with the hydrogens on the periphery.
The general formula for alkanes is CnHn+2 where n is the number of
carbons in the compound.
As larger numbers of carbons and hydrogens combine, the ability
to form isomers arises.
Compounds that have the same molecular formula but different
structural formulas are called isomers.
 The Structure of Organic Molecules: Alkanes and Their Isomers
There are two ways in which molecules that have the formula C4H10 can be
formed.

A condensed structure is a shorthand way of drawing structures in which CC and CH

bonds are understood rather than shown.
 Drawing Organic Structures

A line structure (or line-angle structure) is a

shorthand way of drawing structures in which carbon
and hydrogen atoms are not shown.

A carbon is understood to be wherever a line begins or

ends and at every intersection of two lines.
Hydrogens are understood to be wherever they are
needed to have each carbon form four bonds.
Naming Alkanes
Substituents such as CH3 and CH2CH3, that branch off the
main chain are called alkyl groups. Methyl group: CH3
Ethyl group: CH2CH3
 Naming Alkanes
There are four possible substitution patterns
for carbons attached to four atoms.
A primary (1) carbon atom is a carbon atom
with 1 other carbon attached to it.
A secondary (2) carbon atom is a carbon atom
with 2 other carbons attached to it.
A tertiary (3) carbon atom is a carbon atom
with 3 other carbons attached to it.
A quaternary (4) carbon atom is a carbon atom
with 4 other carbons attached to it.
 Properties of Alkanes
Alkanes contain only nonpolar CC and CH bonds. The only intermolecular
forces influencing them are weak London dispersion forces.
The effect of these forces is shown in the regularity with which the melting
and boiling points of straight-chain alkanes increase with molecular size.
The first four alkanes, methane, ethane, propane, and butane, are gases
at room temperature and pressure.
Alkanes with 515 carbon atoms are liquids.
Alkanes with 16 or more carbon atoms are low-melting, waxy solids.
Alkanes are insoluble in water but soluble in nonpolar organic solvents.
Alkanes are generally less dense than water, they float on its surface.
Mineral oil, petroleum jelly, and paraffin wax are mixtures of higher
alkanes. All are harmless to body tissue and are used in numerous food and
medical applications.
Odorless or mild odor, colorless, tasteless, nontoxic
Nonpolar, insoluble in water but soluble in nonpolar organic solvents, less
dense than water, Flammable, otherwise not very reactive
 Cycloalkanes
A cycloalkane is an alkane that contains a ring of carbon atoms.
To form a closed ring requires an additional CC bond and the loss
of 2 H atoms.
The general formula for cycloalkanes is CnH2n.
Compounds of ring sizes from 3 through 30 and beyond have been
prepared in the laboratory.

The CCC bond angles in cyclopropane are 60, and the bond
angles in cyclobutane are 90, much less than the ideal 109.5
tetrahedral angle.
These compounds are less stable and more reactive than other
cycloalkanes.
Summary of Important Families of Organic Compounds
Summary of Important Families of Organic Compounds
Families of Organic Molecules: Functional Groups
The next four families have functional groups that contain
only single bonds and a carbon atom bonded to an
electronegative atom.
Alkyl halides have a carbonhalogen bond.
Alcohols have a carbonoxygen bond.
Ethers have two carbons bonded to the same oxygen.
Amines have a carbonnitrogen bond.
The next six families contain a carbonoxygen double bond:
aldehydes, ketones, carboxylic acids, anhydrides, esters, and
amides.
The remaining three families have functional groups that
contain sulfur: thioalcohols (known simply as thiols), sulfides,
and disulfides. These play an important role in protein
function.
 Stereochemistry
The branch of chemistry concerned
with the three-dimensional
arrangement of atoms and
molecules and the effect of this on
chemical reactions.
Chemistry in three dimensions
 Isomers are different compounds with the same
molecular formula.
 Review of Isomerism
Isomers Compounds that have the same
molecular formula but do not have identical
structures (Different structural formula).

Constitutional Isomers differ in the way their

atoms are connected.

Stereoisomers compounds with the same

connectivity, different arrangement in space.
Are the following pairs of compounds constitutional isomers or
stereoisomers?
a)
constitutional

b)
constitutional

c)
stereoisomer
Constitutional Isomers and Stereoisomers
Compounds with same molecular formula
 Definitions
Stereoisomers The compounds with the same
connectivity, different arrangement in space.

Enantiomers stereoisomers that are non superimposible

mirror images; only properties that differ are direction
(+ or -) of optical rotation.

Diastereomers stereoisomers that are not mirror images;

different compounds with different physical properties.
Geometric isomers (cis-trans)
Molecules with 2 or more chiral carbons.
 Definitions
Asymmetric center or chiral center sp3 carbon with 4
different groups attached

Optical activity the ability to rotate the plane of

plane polarized light

Chiral compound a compound that is optically active

(achiral compound will not rotate light)

Polarimeter device that measures the optical rotation

of the chiral compound
Diastereomers: Geometric isomers (cis-trans)
With rings and with C=C double bonds, cis-trans notation is
used to distinguish between stereoisomers
Cis identical groups are positioned on the SAME side of a
ring
Trans identical groups are positioned on OPPOSITE sides of a
ring
 Cis-trans Isomers
C-C bonds that are constrained in a cyclic structure can not freely rotate

To maintain orbital overlap in the pi bond, C=C double bonds can not freely rotate.
Diastereomers: Geometric isomers (cis-trans)
Alkenes: Cis-trans isomers are not mirror images, so
these are diastereomers.
H H H CH3
C C C C
H3C CH3 H3C H
cis-2-butene trans-2-butene

Differ in the arrangement of their atoms in space

(cannot interconvert)- Alkenes.
Diastereomers: Geometric isomers (cis-trans)
Ring Compounds: Cis-trans isomers possible. May also have
enantiomers. Example: trans-1,3-dimethylcylohexane
CH3 CH3
H H
H H
CH3 CH3
 Chiral and Achiral Molecules
Although everything has a mirror image, mirror images may
or may not be superimposable.
Some molecules are like hands. Left and right hands are
mirror images, but they are not identical, or superimposable.

A molecule or object that is superimposable on its mirror

image is said to be achiral.
A molecule or object that is not superimposable on its mirror
image is said to be chiral.
 Chirality
Chiral: an object that is not superimposable on its mirror image
Achiral: an object that lacks chirality; one that lacks handedness
We can now consider several molecules to determine whether
or not they are chiral.
 Chirality
The molecule labeled A and its mirror image labeled B are
not superimposable therefore A and B are different
compounds.
A and B are not superimposable stereoisomers, specifically,
they are called enantiomers.
A carbon atom with four different groups is a tetrahedral
stereogenic center or chiral center.
 Chiral Center or Stereogeniccenter
The most common (but not the only) cause of chirality in organic
molecules is a tetrahedral atom, most commonly carbon, bonded to four
different groups
To locate a stereogenic center, examine each tetrahedral carbon atom in
a molecule, and look at the four groups, not the four atoms, bonded to it.
A carbon with four different groups bonded to it is called a chiral center or
stereogenic center.
Always omit from consideration all C atoms that cannot be tetrahedral
stereogenic centers. These include
CH2 and CH3 groups
Any sp or sp2 hybridized C
 Chiral center or Asymmetric center
An asymmetric center is an atom that is bonded to four different
groups.
 Chirality
In general, a molecule with no stereogenic centers will not be
chiral.
With one stereogenic center, a molecule will always be chiral.
With two or more stereogenic centers, a molecule may or may
not be chiral.
An achiral object has at least one element of symmetry, but chiral
molecules do not.
Plane of symmetry: an imaginary plane passing through an
object dividing it so that one half is the mirror image of the
other half
Center of symmetry: a point so situated that identical
components are located on opposite sides and equidistant
from that point along the axis passing through it
 Chirality
An achiral object has at least one element of symmetry, but chiral
molecules do not.
Plane of symmetry: an imaginary plane passing through an
object dividing it so that one half is the mirror image of the other
half
Center of symmetry: a point so situated that identical
components are located on opposite sides and equidistant from
that point along the axis passing through it
Summary of the Basic Principles of Chirality:

Everything has a mirror image. The fundamental question is

whether the molecule and its mirror image are
superimposable.
If a molecule and its mirror image are not superimposable,
the molecule and its mirror image are chiral.
The terms stereogenic center and chiral molecule are related
but distinct. In general, a chiral molecule must have one or
more stereogenic centers.
The presence of a Plane of symmetry or Center of symmetry
makes a molecule achiral.
Classify each of the following pairs as chiral or achiral.
a) CH3 CH3

achiral
CH3 H3C
Cl Br Cl
Br

b) CH3 CH3

chiral
Br Br
Cl Cl H
H

H Br H
Br
c) chiral
F F
 Chiral or Achiral?
2-butanol Asymmetric
center

2-bromopropane

chiral mirror image

A chiral compound and its mirror image are
called enantiomers

achiral
Isomers with one asymmetric center

Draw enantiomers
 Enantiomers
Asparagine: mirror
plane

O OH HO O
C C

H2N C H H C NH2

CH2 CH2
C C
H2N O O NH2

L-asparagine (from D-asparagine (from

asparagus) bitter vetch) sweet taste
taste

enantiomers
Naming enantiomers:
Absolute Configuration (R) ("Rectus" Latin= "right").
and (S) "Sinister" Latin= "left) Configuration.

Both enantiomers of alanine receive the same name in the IUPAC

system: 2-aminopropanoic acid.
Only one enantiomer is biologically active. In alanine only the
enantiomer on the left can be metabolized by the enzyme.
A way to distinguish between them is to use stereochemical
modifiers (R) and (S).
 Absolute Configuration
(R) and (S) Configuration
Assign priorities to the remaining groups based on atomic numbers.
Clockwise (highest to lowest priority) R
Counterclockwise (lowest to highest priority) S

CH 2CH3 1 2
OH HO CH2CH3
H C = C (R)-2-butanol
CH3 CH3
3
 CahnIngoldPrelog Priority System
CahnIngoldPrelog convention is the most widely accepted
system for naming the configurations of chirality centers.

Enantiomers have different spatial arrangements of the four

groups attached to the asymmetric carbon.

The two possible spatial arrangements are called

configurations.

Each asymmetric carbon atom is assigned a letter (R) or (S)

based on its three-dimensional configuration.
 (R) and (S) Configuration: Step 1 Assign Priority
Assign a relative priority to each group bonded to the asymmetric
carbon. Group 1 would have the highest priority, group 2 second, etc.
Atoms with higher atomic numbers receive higher priorities.
I > Br > Cl > S > F > O > N > 13C > 12C > 2H > 1H
Atomic number: F > N > C > H

(R) and (S) Configuration: Breaking Ties

In case of ties, use the next atoms along the chain of each group as
tiebreakers.
 (R) and (S) Configuration: Multiple Bonds

Treat double and

triple bonds as if
each were a bond to
a separate atom.
 (R) and (S) Configuration: Step 2

Working in 3-D, rotate

the molecule so that the
lowest priority group is in
back.
Draw an arrow from
highest (1) to second
highest (2) to lowest (3)
priority group.
Clockwise = (R),
Counterclockwise = (S)
Examples
3
CH3

1
CH3CH 2CH=CH H4
CH2CH 2CH2CH3
2
Counterclockwise
Counterclockwise (S)
(S)
Clockwise
3
(R)
1 CH 2CH3
OH
rotate
C 3 2
C 4
2 CH2CH 3 CH3CH 2CH2 H
CH3CH 2CH2
H OH
4 1
Configuration in Cyclic Compounds
 Absolute Configuration Examples
Determine the absolute configuration of the following
compounds:
 Properties of Enantiomers
Same boiling point, melting point, and density.

Same refractive index.

Rotate the plane of polarized light in the same

magnitude, but in opposite directions.

Different interaction with other chiral molecules:

Active site of enzymes is selective for a specific
enantiomer.
Enantiomers may have different smells.
 Optical Activity
Optical Activity The ability of a compound to rotate
the plane of polarized light.
A compound that rotates the plane of polarization is
said to be optically active.
Chiral compounds are optically active and achiral
compounds are optically inactive.
A polarimeter is used to make such measurements.
 Diastereomers
Molecules with more than one chirality center have mirror image stereoisomers
that are enantiomers
In addition they can have stereoisomeric forms that are not mirror images, called
diastereomers

Diastereomers
Epimers
 Meso Compounds
Tartaric acid has two chirality
centers and two diastereomeric
forms
One form is chiral and the other is
achiral, but both have two chirality
centers
An achiral compound with chirality
centers is called a meso
compound it has a plane of
symmetry
The two structures on the right in
the figure are identical so the
compound (2R, 3S) is achiral
Enantiomers Meso
Racemic Mixtures &The Resolution of Enantiomers

A 50:50 mixture of two chiral compounds that are mirror images

does not rotate light called a racemic mixture (named for
racemic acid that was the double salt of (+) and (-) tartaric acid
The pure compounds need to be separated or resolved from the
mixture (called a racemate)
To separate components of a racemate (reversibly) we make a
derivative of each with a chiral substance that is free of its
enantiomer (resolving agent)
This gives diastereomers that are separated by their differing
solubility
The resolving agent is then removed
Resolution of Enantiomers

Inseparable
by normal
extraction
techniques
due to
identical
chemical
properties
Resolution of Enantiomers

Separable
by normal
extraction
techniques
due to
different
chemical
properties
Physical Properties of StereoisomersOptical Activity

The chemical and physical properties of two enantiomers

are identical except in their interaction with chiral
substances. They have identical physical properties,
except for how they interact with plane-polarized light.

Plane-polarized (polarized) light is light that has an electric

vector that oscillates in a single plane. Plane-polarized
light arises from passing ordinary light through a polarizer.

A polarimeter is an instrument that allows polarized light to

travel through a sample tube containing an organic
compound. It permits the measurement of the degree to
which an organic compound rotates plane-polarized light.
 Chiral compounds are optically active
Plane-polarized light is produced by passing normal light
through a polarizer. A polarizer or polariser is an optical
filter that lets light waves of a specific polarization pass and
blocks light waves of other polarizations. It can convert a
beam of light of undefined or mixed polarization into a beam
of well-defined polarization, that is polarized light.
 Optical Activity

When plane-polarized light passes through a solution of achiral

molecules, the light that exits the sample tube remains
unchanged. A compound that does not change the plane of
polarized light is said to be optically inactive.
 Optical Activity
However, when plane-polarized light passes through a
solution of a chiral compound, the plane of the polarized
light is rotated through an angle . The angle is
measured in degrees (), and is called the observed
rotation. A compound that rotates polarized light is said
to be optically active.
 Measurement of Optical Rotation
A polarimeter measures the rotation of plane-polarized that has
passed through a solution
The source passes through a polarizer and then is detected at a
second polarizer
The angle between the entrance and exit planes is the optical
rotation.
 The rotation of polarized light can be clockwise or
anticlockwise.
If the rotation is clockwise (to the right of the noon
position), the compound is called dextrorotatory. The
rotation is labeled d or (+).
If the rotation is counterclockwise, (to the left of noon),
the compound is called levorotatory. The rotation is
labeled l or (-).
Two enantiomers rotate plane-polarized light to an equal
extent but in opposite directions. Thus, if enantiomer A
rotates polarized light +5, the same concentration of
enantiomer B rotates it 5.
No relationship exists between R and S prefixes and the
(+) and (-) designations that indicate optical rotation.
Physical Properties of Stereoisomers Racemic Mixtures

An equal amount of two enantiomers is called a racemic

mixture or a racemate. A racemic mixture is optically inactive.
Because two enantiomers rotate plane-polarized light to an
equal extent but in opposite directions, the rotations cancel,
and no rotation is observed.
 Specific rotation
Specific rotation is a standardized physical constant for
the amount that a chiral compound rotates plane-
polarized light. Specific rotation is denoted by the
symbol [] and defined using a specific sample tube
length (l, in dm), concentration (c in g/mL), temperature
(25 0C) and wavelength (589 nm).
Physical Properties of StereoisomersOptical Purity

Enantiomeric excess (optical purity) is a measurement of

how much one enantiomer is present in excess of the
racemic mixture. It is denoted by the symbol ee.

ee = % of one enantiomer - % of the other enantiomer.

Consider the following exampleIf a mixture contains 75%
of one enantiomer and 25% of the other, the enantiomeric
excess is 75% - 25% = 50%. Thus, there is a 50% excess of
one enantiomer over the racemic mixture.
The enantiomeric excess can also be calculated if the
specific rotation [] of a mixture and the specific rotation []
of a pure enantiomer are known.
ee = ([] mixture/[] pure enantiomer) x 100.
 Since enantiomers have identical physical properties, they cannot be
separated by common physical techniques like distillation.
Diastereomers and constitutional isomers have different physical
properties, and therefore can be separated by common physical
techniques.

The physical properties of

the three stereoisomers
of tartaric acid
Example: A compound was isolated in the lab and the
observed roation was +10 when measured in a 1 dm.
tube containing 1.0 g of sample in 10 mL of water. What
is the specific rotation of this compound?

[] = /(length x (g/ml));

[] = 10/(1dm. X (1.0g/10ml)) = +100

Example: What is the ee of the given racemic mixture?

95% A and 5% B
ee = % of A - % of B
= 95 5 = 90 ee
Example: Given the ee value, what percent is there of
each isomer, 60% ee

60% excess A, then 40% racemic mixture

(so 20% A and 20% B)

So, 60% + 20% = 80% A and leaves 20% B

Example: A pure compound has a specific rotation of

+24, a solution of this compound has a rotation of +10,
what is the ee?

ee = [] of mixture / [] of pure x 100

=+10/+24 x 100 = 42%
 Specific Rotation and Molecules
Characteristic property of a compound that is optically active the
compound must be chiral

The specific rotation of the enantiomer is equal in magnitude but

opposite in sign

94
 Pasteurs Discovery of Enantiomers
Louis Pasteur discovered that sodium ammonium salts of tartaric
acid crystallize into right handed and left handed forms
The optical rotations of equal concentrations of these forms have
opposite optical rotations
The solutions contain mirror image isomers, called enantiomers
and they crystallized in distinctly different shapes such an event
is rare
Chemical Properties of Enantiomers
Two enantiomers have exactly the same chemical properties
except for their reaction with chiral non-racemic reagents.
Many drugs are chiral and often must react with a chiral
receptor or chiral enzyme to be effective. One enantiomer of
a drug may effectively treat a disease whereas its mirror
image may be ineffective or toxic.