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CHAPTER 7

STREOCHEMISTRY
CHIRALITY
• Chiral – not identical with its mirror image – nonsuperimposable mirror
image

• Achiral – has superposable on their mirror images


Streoisomers with one chiral Carbon Atom
• Assymeric carbon – 4 different gp’s bonded to the
carbon

• Chirality center
•Physical properties: MP, BP and refractive
point are identical.
•They differ in direction in the plane polarized
light.
•Right – dextrorotatory (D): left –levorotatory
(L)
•50/50 mixture of enantiomers – racemic
mixture
•Molecules (nonsuperimposable, produce
measurable rotation in plane polarized light)
=chiral molecule or optically active.
How to express the
configuration of
enantiomers in 3D??
4) A tetrahedral model of a
chiral carbon atom (3
atoms will be a ‘base” of
the pyramid.
5) Rotate the model upward,
so 2 atoms are sticking
out toward you
horizontally and other 2
atoms are directed
vertically away from you.
6) The 2 horizontal atoms –
wedges. projected out of
the paper
7) The 2 vertical atoms –
dashes. projected behind
the plane of paper.
Stereoisomers With Two Different
Chiral Carbon Atoms

Van’t Hoff rule : 2n


12 and 34 are enantiomers
13,14, 23, 24 are diastreoisomers (stereoisomers that
are not mirror image)
Molecules with two similar Chiral
Carbon Atoms

180o
Meso compound
Streoisomerism in Cyclic compound
• Cis isomer = meso compound

• Trans isomer = enantiomeric compound


Specific Configuration
R and S designation – Cahn-Ingold-Prelog
System
3) Groups connected to the chiral carbon are assingned priorities (atomic
number)
4) Lowest priority is put directed away from the observer. The remain 3
groups are projected toward the observer.
5) If the molecule moves in clockwise – R; counterclockwise - S
Determining Group Priorities
Cl
H2
I C H2C C CH2 Br

CH2

CH2

CH3

Cl > CH2Br > CH2CH2I > CH2CH2CH3

If rotates clockwise – R; anticlockwise = S


How to determine R and S configuration
Streoisomerism in Chemical Reaction
• Meso Compound – hydroxylation and
hydrogenation
• A pair of Enantiomers
• A pair of diastreoisomers