Intro Org 2024

INTRODUCTORY ORGANIC CHEMISTRY
Prepared by :
Miss Bwalya
Stereochemistry
&
Chiral Molecules
Stereochemistry
• stereochemistry is the three-dimensional structure of a
molecule.
• As a consequence of stereochemistry, apparently minor
differences in 3-D structure can result in vastly different
properties. We can observe this by considering starch and
cellulose, which are both composed of the same repeating
unit.
Stereochemistry of Carbohydrates
Two Major Classes of Isomers
• isomers are different compounds with the same

molecular formula.
• The two major classes of isomers are constitutional
isomers and stereoisomers.
• Constitutional isomers have different IUPAC names,

the same or different functional groups, different
physical properties and different chemical properties.
• Stereoisomers differ only in the way the atoms are

oriented in space. They have identical IUPAC names
(except for a prefix like cis or trans and E or Z). They
always have the same functional group.
Configurational Isomers
• Configurational isomers have a particular three-

dimensional arrangement of atoms called a
configuration.
• Configuration is the spatial array of atoms that
distinguishes stereoisomers.
• Configurational isomers are stereoisomers that

differ in configuration.
Constitutional Isomers vs Stereoisomers
TRY THESE!!!!!!
Chirality or Handedness
• 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.
Achiral Objects and Molecules
• Other molecules are like

socks. Two socks from a pair
are mirror images that are
superimposable. A sock and
its mirror image are identical.
• A molecule or object that is
superimposable on its mirror
image is said to be achiral.
(you can wear it on either foot!)
Achiral Molecules
• Do these molecules conatain a Plane of Symmetry (Mirror Plane)?
Chiral Molecules
• The molecule labeled A and its mirror image labeled B
are not superimposable. No matter how you rotate A and
B, all the atoms never align. Thus, CHBrClF is a chiral
molecule, and A and B are different compounds.
• A and B are stereoisomers—specifically, they are
enantiomers.
• A carbon atom with four different groups is a tetrahedral
stereogenic center.
Chiral vs Achiral
• In general, a molecule with no stereogenic centers will
not be chiral. There are some exceptions.
• With one stereogenic center, a molecule will always be
chiral.
• With two or more stereogenic centers, a molecule may or
may not be chiral, e.g. Meso compound (contains a plane
of symmetry or a mirror plane)
• Achiral molecules contain a plane of symmetry but chiral
molecules do not.
• A plane of symmetry is a mirror plane that cuts the
molecule in half, so that one half of the molecule is a
reflection of the other half.
Plane of Symmetry
or
Mirror Plane
Chiral vs Achiral
Stereogenic Centers
• To locate a stereogenic center, examine the four
groups—not the four atoms—bonded to each tetrahedral
carbon atom in a molecule.
• Omit from consideration all C atoms that cannot be
tetrahedral stereogenic centers. These include
• Methylene and methyl units, i. e. CH2 and CH3 groups
respectively.
• Any sp or sp2 hybridized Carbons, e.g. triple bonds, and
double bonds in alkenes (C=C) and carbonyls (C=O).
Number of Stereogenic Centers in a Molecule
• Larger organic molecules can have two, three or even
hundreds of stereogenic centers.
Enantiomers
Enantiomers
One of a pair of molecular species that

are mirror images of each other and
not superposable.
They are mirror-image stereoisomers.
Drawing Enantiomers
• To draw both enantiomers of a chiral compound such as

2-butanol, use the typical convention for depicting a
tetrahedron: place two bonds in the plane, one in front of
the plane on a wedge, and one behind the plane on a
dash. Then, to form the first enantiomer, arbitrarily place
the four groups—H, OH, CH3 and CH2CH3—on any bond
to the stereogenic center. Then draw the mirror image.
Pairs of Enantiomers
Stereogenic Centers in a cyclic Alkane
• Stereogenic centers may also occur at carbon atoms

that are part of a ring.
• To find stereogenic centers on ring carbons, always
draw the rings as flat polygons, and look for tetrahedral
carbons that are bonded to four different groups.
Enantiomers of 3-methylcyclohexene
• In 3-methylcyclohexene, the CH3 and H substituents that

are above and below the plane of the ring are drawn with
wedges and dashes as usual.
Enantiomers of Biomolecules
• Many
biologically
active
molecules
contain
stereogenic
centers on
ring carbons.
Polycyclic Ethers
• How many stereogenic centers are in this
polycyclic ether structure?
O
H
O H
H
H
O
H H
O
Me
H O
H
HO
H OH O
H
R/S Isomers
Labeling Stereogenic Centers with R or S
• Since enantiomers are two different compounds, they
need to be distinguished by name. This is done by
adding the prefix R or S to the IUPAC name of the
enantiomer.
• Naming enantiomers with the prefixes R or S is called
the Cahn-Ingold-Prelog system.
• To designate enantiomers as R or S, priorities must be
assigned to each group bonded to the stereogenic
center, in order of decreasing atomic number. The atom
of highest atomic number gets the highest priority (1).
Priority Rules for Naming Enantiomers (R or S)
• If two atoms on a stereogenic center are the same,

assign priority based on the atomic number of the atoms
bonded to these atoms. One atom of higher priority
determines the higher priority.
Priority of Isotopes on a Stereogenic Center
• If two isotopes are bonded to the stereogenic center,

assign priorities in order of decreasing mass number.
Thus, in comparing the three isotopes of hydrogen, the
order of priorities is:
Priority Rules for Multiple Bonds in (R or S) Labeling
• To assign a priority to an atom that is part of a multiple bond,
treat a multiply bonded atom as an equivalent number of
singly bonded atoms. For example, the C of a C=O is
considered to be bonded to two O atoms.
• Other common multiple bonds are drawn below:

Examples Assigning Priorities
Cahn-Ingold-Prelog System for
Naming Enantiomers R or S
R or S Enantiomers
Positioning the Molecule for R/S Assignment
R-enantiomer (Clockwise Rotation)
S-enantiomer (Counterclockwise Rotation)
Manipulation of Chiral Molecules
Switching any two groups on a molecule with a
single stereogenic center, converts the
molecule into its enantiomer.

Intro Org 2024

Uploaded by

Copyright:

Available Formats

Intro Org 2024

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Intro Org 2024

Uploaded by

Copyright:

Available Formats

INTRODUCTORY ORGANIC CHEMISTRY

• isomers are different compounds with the same

• Constitutional isomers have different IUPAC names,

• Stereoisomers differ only in the way the atoms are

• Configurational isomers have a particular three-

• Configurational isomers are stereoisomers that

• Although everything has a mirror image, mirror images

• Other molecules are like

One of a pair of molecular species that

• To draw both enantiomers of a chiral compound such as

• Stereogenic centers may also occur at carbon atoms

• In 3-methylcyclohexene, the CH3 and H substituents that

• If two atoms on a stereogenic center are the same,

• If two isotopes are bonded to the stereogenic center,

• Other common multiple bonds are drawn below:

You might also like

Pfad - The Proxy pFad of © 2024 Garber Painting. All rights reserved.