Stereochemistry

By: Isman Kurniawan

Friday, June 20, 14

Stereochemistry
Stereoisomers

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Chirality
Objects that have left-handed and righthanded forms are called chiral

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Chirality
Chirality and enantiomerism in organic
molecules

Enantiomers : nonsuperimposable mirrorimage molecules

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Chirality
Asymmetric carbon atoms
Assymmetric/chiral carbon atom : carbon
atom that is bonded to four different
groups

Friday, June 20, 14

Chirality
Asymmetric carbon atoms

Friday, June 20, 14

Chirality
Asymmetric carbon atoms
If a compound has no asymmetric carbon
atom, it is usually achiral.

If a compound has just one asymmetric

carbon atom, it is chiral.

If a compound has more than one

asymmetric carbon, it may or may not be

chiral.

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Exercise
Draw a 3D structure for each compound

and star all asymmetric carbon atoms.

Draw the mirror image for each structure.

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Chirality
Mirror planes of symmetry
Any molecule that has an internal mirror
plane of symmetry cannot be chiral.

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(R) and (S) Nomenclature of

Asymmetric Carbon Atoms

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(R) and (S) Nomenclature of

Asymmetric Carbon Atoms
Chan-Ingold-Prelog convention
1. Assign a priority to each group bonded
to the asymmetric carbon.
a. Atoms with higher atomic numbers
receive higher priorities.

Friday, June 20, 14

(R) and (S) Nomenclature of

Asymmetric Carbon Atoms
Chan-Ingold-Prelog convention
1. Assign a priority to each group bonded
to the asymmetric carbon.
b. In case of ties, use the next atoms
along the chain of each group as
tiebreakers

Friday, June 20, 14

(R) and (S) Nomenclature of

Asymmetric Carbon Atoms
Chan-Ingold-Prelog convention
1. Assign a priority to each group bonded
to the asymmetric carbon.
c. Treat double and triple bonds as if
each were a bond to a separate atom

Friday, June 20, 14

(R) and (S) Nomenclature of

Asymmetric Carbon Atoms

Chan-Ingold-Prelog convention
2. Using a three dimensional drawing, put
the fourth priority group in back.
3. Draw an arrow from the first priority
group, through second, to the third.

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(R) and (S) Nomenclature of

Asymmetric Carbon Atoms
Chan-Ingold-Prelog convention

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Exercise
Draw the enantiomer of 1,3-

dibromobutane and label them as (R) and

(S).

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Exercise
Star (*) each asymmetric carbon atom in

the following examples and determine

whether it has the (R) or (S) configuration.

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Optical Activity
Polarimetry

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Optical Activity
Polarimetry
Compound that rotate plane of polarized
light toward the right are called
dextrorotatory (d)/(+).

Compound that rotate plane of polarized

light toward the left are called
levorotatory (l)/(-).

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Fischer Projections
Drawing Fischer projections
Uses a cross to represent an asymmetric
carbon atom.

The horizontal lines project toward the

viewer, and the vertical lines project away

from the viewer.

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Fischer Projections
Drawing Fischer projections

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Exercise
Draw a Fischer projection for each
compound

a. (S)-1,2-propanediol
b. (R)-2-butanol

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Assignment
1. Star (*) any asymmetric carbon atoms.
Label each asymmetric carbon as (R) or (S).

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Assignment
2. Convert the following perspective formula
to Fischer projections

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Assignment
3. Convert the following Fischer projections
to perspective formulas

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Assignment

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Deadline : June 25th 2014