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ISOMERS

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.

Skeletal-different arrangement of carbon atoms


e.g. n-butane and 2-methylpropane

Positional-different position of functional groups


e.g. 1-Butanol and 2-Butanol

Functional-different functional groups present


e.g. Propanal and 2-Propanone

2. Stereoisomers
Compounds that have the same molecular formula, same
arrangement of bonded atoms but different orientation in space.

2.1Enantiomers-a pair of compounds that are non-superimposable


mirror images
e.g. (R)-2-Bromobutanol and (S)-2-Bromobutanol

2.2Diastereomers- Non-mirror-image stereoisomers


2.2.1 Geometric
e.g. cis-2-butene and trans-2-butene

2.2.2 Configurational
e.g. (2R, 3S)-2,3-Dibromobutane and
(2R, 3R)-2,3-Dibromobutane
II. Enantiomers and Chiral molecules

Chiral Molecule- not superimposable with its mirror image


e.g (R)-2-Bromobutane

Achiral Molecule-not chiral, it has a plane of symmetry. ( A plane of


symmetry bisects a molecule so that one half of the molecule is the
mirror image of the other.)
e.g. Methane

Stereogenic center/chiral carbon/assymetric carbon- carbon that bears


four different substituents
CH2CH3

C chiral carbon
H
Br
e.g. CH3

Test for Chirality


1. If a compound has no chiral carbon, it is usually achiral
2. If a compound has just one chiral carbon, it is chiral
3. If a compound has more than one chiral carbon, it may or may not
be chiral

Enantiomers have identical properties except


1. for the directions of rotation of the plane of polarized light.
2. for their behavior toward optically active reagents.

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.

Polarimeter- device used to measure optical activity


Polarizer Sample
Tube

light plane analyser


source polarized
light
Specific Rotation []D is a physical property expressing optical activity

[]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

IV. Absolute Configuration


Actual arrangement of atoms in space.
The three-dimensional arrangement of atoms bonded to a stereocenter.

A. Nomenclature of Enantiomers: Cahn-Ingold-Prelog system or


R/S system (from latin words Rectus and Sinister meaning right
and left respectively).

B. No necessary correlation exists between the (R) and (S)


designation and the direction of rotation of plane of polarized
light.
Examples:

(R)-(+)-2-Methyl-1-butanol and (S)-(-)-2-Methyl-1-butanol

(R)-(-)-1-Chloro-2-methylbutane and (S)-(+)-1-Chloro-2-


methylbutane
V. Racemic Mixture (Racemates)]
Mixture containing equal quantities of Enantiomers.
A 50:50 mixture of Enantiomers. Net rotation is zero.

VI. Meso compound- a compound that contains stereocenters but is achiral


because it has a plane of symmetry.

VII. Naming Stereoisomeric Alkenes: E-Z system


From the German words entgegen and zusammen meaning together
and opposite respectively.

VIII. Three-D representations of molecules.

Perspective views.

C C

C C

Fischer Projection

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