Paaras Thakur

Stereochemistry

L-7

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Example Tell whether the two structures in each pair represent enantiomers or two molecules
of the same compound in different orientations.
(R) and (S) Nomenclature of Chiral Carbon Atoms
Example Find R/S configuration of following compounds.
 Racemic Mixture

An equimolar mixture of two enantiomers is called a racemic mixture (or

racemate or racemic form). A racemic mixture causes no net rotation of plane -
polarized light.
Racemic Mixture

A reaction that uses optically inactive reactants and catalysts cannot

produce a product that is optically active. Any chiral product must be formed
as a racemic mixture.
Racemic Mixture
Newman to Fischer Projection
 Newman to Fischer Projection

We must always keep the Fischer projection formulas in the plane of the paper,
and we are not allowed to flip them over.
 Biological Discrimination of Enantiomers

Enzymes in living systems are chiral, and they are capable of distinguishing
between enantiomers. Usually, only one enantiomer of a pair fits properly into the
chiral active site of an enzyme.
 Biological Discrimination of Enantiomers

Even your nose is capable of distinguishing between some enantiomers.

 More than one Chirality Center

Let us consider the stereoisomers of 3-chlorobutan-2-ol

 More than one Chirality Center

When a molecule has two chirality centres, and each can be R or S , four
stereoisomers are normally possible: RR , SS , RS , and SR .
 Enantiomers and Diastereomers

Let us examine stereoisomers of 2,3,4-trihydroxybutanal as a typical example of a

compound with two chirality centres.

Carbons C2 and C3 are the chirality centres and we can represent the four
stereoisomers, (2 R ,3 R ), (2 S ,3 S ), (2 R ,3 S ), and (2 S ,3 R ), by Fischer
projections.
Enantiomers and Diastereomers
Example Draw all possible stereoisomers for 2-bromo-4-chloropentane.
Example Find relationship between the given pairs.
Example Which Fischer projection represents the given wedge dash structure :
Example Which has D configuration.
Example Which is not the pair of enantiomers ?
Example How are compounds I and II related ?
 Meso Compounds

A meso compound is one whose molecules are superimposable on their mirror

images even though they contain chiral centres. A meso compound is optically
inactive since it has a plane of symmetry. A meso compound is non-resolvable.

Let us consider the stereoisomers of 2, 3-dibromobutane

Meso Compounds
Meso Compounds
Example Determine which of the following compounds are chiral. Star any asymmetric
carbon atoms, and draw in any mirror planes. Label any meso compounds.
Example
Example State how each pair of compounds is related. Are they enantiomers, diastereomers,
constitutional isomers, or identical?
Example State how each pair of compounds is related. Are they enantiomers, diastereomers,
constitutional isomers, or identical?
Example Which of the following are chiral :
Example Which of the following are chiral :
Example
Example Which of the given statement(s) about N, O, P and Q with respect to M is (are)
correct?
Example
Example
Example
Example
Example
Example
If optical rotation produced by is + 36º then that produced by

is

A. –36º
B. 0º
C. +36º
D. unpredictable
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