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Constitutional Stereoisomers
Isomers
Diastereomers Enantiomers
Cis-Trans Configurational
Diastereomers Diastereomers
ORGANIC CHEMISTRY
SUPPLEMENTARY NOTES:
ISOMERS
I. Isomers (from Greek isos + meros meaning made of the same parts)
Compounds with the same molecular formula but are not identical
1. Constitutional (Structural)
Compounds with the same molecular formula but have different
arrangement (connectivity) of bonded atoms.
2. Stereoisomers
Compounds that have the same molecular formula, same
arrangement of bonded atoms but different orientation in space.
2.2.2 Configurational
e.g. (2R, 3S)-2,3-Dibromobutane and
(2R, 3R)-2,3-Dibromobutane
II. Enantiomers and Chiral molecules
C chiral carbon
H
Br
e.g. CH3
e.g.
(+)-2-Methyl-1-butanol (-)-2-Methyl-1-butanol
Specific rotation +5.90o -5.90o
Boiling point 128.9oC 128.9oC
Relative density 0.8193 0.8193
Refractive index 1.4107 1.4107
III. Optical Activity
Ability of a molecule to rotate the plane of polarized light.
Molecules that exhibit optical activity are said to be optically active.
Polarizer Sample
Tube
[]t = /cl
where = observed rotation
c = concentration of the sample in grams per mL of solution
l = length of polarimeter tube in decimeters (1dm=10cm)
= wavelength (usually the sodium D-line having a wavelength
of 589 nm)
t= temperature
Perspective views.
C C
C C
Fischer Projection