Topic 07 Stereochemistry

Stereochemistry
Chem21a: Topic 7
Prepared by: Annie Rhiz J. Destura, RCh, MSc
Stereochemistry
•Chirality and Stereocenters

•Stereoisomers
*Enantiomers
Cahn-Ingold-Prelog Convention (R/S)
Optical Activity
*Diasteriomers
Cis-trans
E/Z system
*Fischer Projections
Chirality and Stereocenters
Stereoisomers are subdivided into two (2) groups
1. ENANTIOMERS
2. DIASTEREOMERS
Enantiomers and Diastereomers
ASSIGNMENT!!!
Non Superposable
Chiral
Centers
• If a compound and its mirror image can be superim
posed then it is called an ACHIRAL COMPOUND.
ASSIGNMENT!!!
How to Test for Chirality: Planes of Symmetry
Enantiomeric pairs are compounds that have the
same Molecular Formula, Attachments of Atoms but
differ in 3D orientation which results to different
properties.
Enantiomeric pairs can be name using the

Cahn-Ingold-Prelog System or also known as the
R and S Configuration.
R means “Rectus” or Right

S means “Sinister” or Left
(c) (b)
(c) (b)
ASSIGNMENT!!!
Pair of Enantiomers
S - Configuration R - Configuration
Same Compounds
R - Configuration R - Configuration
Pair of Enantiomers
S - Configuration R - Configuration
• When a compound has only 1 chiral center,
then its no. of stereoisomers will be two (2)
• When a compound has 2 chiral centers,
then its no. of stereoisomers will be four (4)
• When a compound has 3 chiral centers,
then its no. of stereoisomers will be nine (8)
The number of chiral centers indicate the

no. of possible enantiomers which is denoted by
no. of stereoisomers = 2n
n = no. of Chiral centers
Pair of Pair of
Enantiomers Enantiomers
Diastereomers
Diastereomers
No
No
Diastereomers
Pair of Pair of
Diastereomers
Pair of Pair of
Diastereomers
Pair of Pair of
Diastereomers
Pair of Pair of
No. of stereoisomers =
2n, n = 2.
So,
No. of stereoisomers = 4
Pair of
Enantiomers
Plane of
Symmetry
Same Compound
Meso Compound – Contains a plane of symmetry

• Therefore, 2,3-dibromobutane has only 3
stereoisomers.
Pair of The same

Enantiomers compound
ASSIGNMENT!!!
Diastereomers
• Stereoisomers whose molecules are not mirror images of ea

ch other.
• Cis/trans isomers are classified as diastereomers.
cis isomers – substituents are on the same side.
trans isomers – substituents are on the opposite side.
• For cycloalkanes, cis-trans isomers can be easily detected.
• For aliphatic hydrocarbons or straight chains, cis-trans isom
ers can be distinguished when there is a double bond
But-2-ene
Possible Line-Bond Structures:
Cis-but-2- trans-but-2-
ene ene
• Cis/trans naming for double bonds are applicable on simple
alkenes and contains one substituent at each carbon.
Example:
What if we have a double bond but the substituents are different?

Example: 2-chloro-4-methylpent-2-ene
• We cannot use cis/trans naming here because it is
ambiguous in naming specially for these cases of alkenes.
• Instead we use the (E)-(Z) system.
E- system: both groups are on different sides.
Z – system: both groups are the same sides.
• (E)-(Z) system is used for naming complicated alkenes.
• How to name alkenes using the (E)-(Z) system?
Step 1: Label the carbons with the double bond as C1 and C2

Step 2: Prioritize the groups attached to each carbon, C1 and C2.
(a) The group with the highest priority will be based in their
atomic number. High atomic number, no.1 priority.
(b) If the atoms attached directly to the same carbon are the
same, move to the next atom attached to it until you find a
difference in the atomic number.
(Z)
conformation
1 2
(Z)-2-chloro-4-methylpent-2-ene
ASSIGNMENT!!!
Fischer Projection Formulas
• What is this?
This is another way of viewing molecules from a
3D structure to a 2D structure.
• How to do this?
Top
View
Fischer
Projection
• Since all bonds are sigma bonds, then the bonds can be
rotated.
• These are the allowed rotations for the Fischer projection.
Hold this
part here
• Since all bonds are sigma bonds, then the bonds can be
rotated.
• These are the allowed rotations for the Fischer projection.
Hold this
part here
ASSIGNMENT!!!
Lets draw the Fischer Projection Formula for

the following structuress:
Thank You
References
Morrison, R.T and Boyd, R.N., Organic Chemistry, 6th edition, ISBN-13: 97
8-0136436775.
Mcmurry, J. ,et al., Fundamentals of General, Organic, and Biological Che
mistry, 6th edition, Prentice Hall, 2010.
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Stereochemistry

•Chirality and Stereocenters

Enantiomeric pairs can be name using the

R means “Rectus” or Right

The number of chiral centers indicate the

Meso Compound – Contains a plane of symmetry

Pair of The same

• Stereoisomers whose molecules are not mirror images of ea

Possible Line-Bond Structures:

What if we have a double bond but the substituents are different?

Step 1: Label the carbons with the double bond as C1 and C2

Lets draw the Fischer Projection Formula for

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