STEREOISOMERS

Types of isomers
 Stereoisomers

Molecules with

the same molecular and structural formula,

but with

different spatial arrangements of atoms.

 Types of stereoisomers

● Geometrical isomers ● Optical isomers

– Cycloalkanes
– Linear alkenes

cis - trans right (+) - left (-)

 Cycloalkanes

Cis
substitutes on the same side of plane

Trans
substitutes on opposite sides of plane
 Cyclopropane

Geometry does not allow rotation of single bonds

1,2-dichlorocyclopropane
1,2-dichlorocyclobutane

The same happens with 1,2-dimethylcyclopropane

 Substituted alkenes

Cis
substitutes on the same side of double bond

Trans
substitutes on opposite sides of double bond
1,2-dichloroethene
2-butene
Geometrical isomers rule
Trans isomer is more stable
 Trans fatty acids => higher b.p.

More linear => more dense packing => stronger V.d.Waals => higher b.p.
Cis alkenes => higher b.p.

Net polarity => dipole-dipole forces => higher b.p.

 but-2-ene-1,4-dioic acid

Cis-isomer reacts more easily (at lower temperature)

cis & trans platin
Cis-platin = anti-cancer drug

Binds to DNA of cancer cells and blocks reproduction

Optical isomers

Images cannot get superimposed

Mirror images = enantiomers
 Chiral = enantiomers exist

Chiral center =
an atom bonded to four different groups of atoms

If there is a chiral center =>

Molecule is chiral=>

Enantiomers exist
Chiral molecules
Non-chiral molecules
Polarized light
Polarimeter
 Enantiomers and rotation

Enantiomers rotate plane of polarization in different directions

Racemic mixtrure

Ratio
of
enantiomers

50% - 50%
 Chemical properties

Enantiomers react differently with other optically active compounds

Thalidomide
 Aspartame

L-aspartame = sweet R-aspartame = bitter

Sn2 – complete inversion
Sn1 – racemic mixture
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