Stereochemistry

By

Ass. Prof. Abdelreheem Abdelfatah Saddik

Lecturer of Materials Science, Chemistry Department,

faculty of science, Assiut University

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Lecture 4
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‫امتحان أعمال السنة سيكون االسبوع‬
‫القادم ‪ ،10/11/2021‬وال اعذار اال‬
‫اعذار مرضية‬

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 Mention the optically active molecules and their absolute configuration.

Give the name of the following with mentioning the configuration.

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Mention the optically active molecules and their absolute configuration.

Give the name of the following with mentioning the configuration.

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 Diastereoisomers (Diastereomers) Important
Diastereomers: are stereoisomers that are not mirror images of one another and are
non-superimposable on one another. They have different chemical and physical
properties including meso compounds, cis–trans, E-Z, and non-enantiomeric optical
isomers. Molecules possessing more than one stereogenic centre exhibit
diastereoisomerism if the configuration at one or more of the sterogenic centre is
different, while others are same.
Plane of symmetry

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 Epimers Important
o An epimer is one of a pair of stereoisomers. The two isomers differ in
configuration at only one stereogenic centre. All other stereocentres in the
molecules are the same in each.
o Epimerization is the process of forming an epimer by changing one asymmetric
centre in a compound that has more than one.

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Anomers Important
o Anomers and epimers are both diastereomers, but an epimer is a stereoisomer that
differs in configuration at any single stereogenic center, while an anomer is
actually an epimer that differs in configuration at the acetal/hemiacetal carbon.

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Glucose

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o A molecule possessing n stereogenic centres has a maximum of: 2n stereoisomers.
Molecular symmetry within the molecule may result in a reduction of the
numbers of different isomers due to internal compensation. Example: 2,3,4-
Trihydroxybutanal.
Important
H H H H
HO OH Enantiomers HO OH

HOH2C CHO HOH2C CHO

2R, 3R 2S, 3S

Diastereoisomers Diastereoisomers Diastereoisomers

H OH HO H
HO H Enantiomers H OH

HOH2C CHO HOH2C CHO

2S, 3R 2R, 3S
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How many possible stereoisomers of these compounds:

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Erythro-, Threo- and Meso-Nomenclature Important
• Erythro-, Threo- are applied to systems containing two asymmetric carbons when
two of the groups are the same and the third is different.

• Erythro- describes adjacent stereocentres possessing similar or identical substituents

on the same side of the vertical axis of the Fischer projection

• Threo- describes adjacent stereocentres possessing similar or identical substituents

on the opposite side of the vertical axis of the Fischer projection

Y CHO Y CHO

X W H OH W X HO H

X W H OH X W H OH

Z CH2OH Z CH2OH

Erythro- D-Erythrose Threo- D-Threose

stereocentres stereocentres
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Meso Compounds
Y CO2H
• A meso compound is an achiral compound
X W H OH
(superimposable on its image) that contains
X W H OH
more than one stereogenic center.
Y CO2H
• Meso compounds generally contain a
Meso-stereocentres Meso-Tartaric Acid
plane of symmetry so that they possess two
mirror image halves.
Important

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 D and L Assignments
CHO COOH
H * OH H2N * H
CH2OH CH2CH2COOH
D-(+)-glyceraldehyde L-(+)-glutamic acid

Penultimate carbon is the stereocenter farthest away from the carbonyl group. If
the higher priority group is on the left, then (L), if on the right then (D) sugar.

Important

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