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01 Stereochemistry

1. Constitutional isomers have different connectivity of atoms and different IUPAC names, while stereoisomers have the same connectivity but different 3D orientations. 2. Chiral molecules have one or more stereocenters and lack reflective symmetry, while achiral molecules have no stereocenters or multiple stereocenters. 3. Enantiomers are non-superimposable mirror images of each other and rotate plane-polarized light in opposite directions.

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142 views6 pages

01 Stereochemistry

1. Constitutional isomers have different connectivity of atoms and different IUPAC names, while stereoisomers have the same connectivity but different 3D orientations. 2. Chiral molecules have one or more stereocenters and lack reflective symmetry, while achiral molecules have no stereocenters or multiple stereocenters. 3. Enantiomers are non-superimposable mirror images of each other and rotate plane-polarized light in opposite directions.

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2302169 Chem Med Studt

1) Constitutional (Structural) Isomer VS Stereoisomer

STEREOCHEMISTRY

Constitutional isomer Stereoisomer -different IUPAC names -identical IUPAC names (except for a prefix like cis or trans) -same or different functional groups -same functional group(s) -different physical & chemical properties -different only in orientation in space (3D; configuration)

2) Stereochemistry

3) Chiral VS Achiral Molecule 3.1 Chiral molecule: Molecule or object that is not superimposible on its mirror image Chiral Achiral

2302169 Chem Med Studt


One stereogenic center (chiral center)

STEREOCHEMISTRY

No plane of symmetry

0 chiral center achiral molecule 1 chiral center chiral molecule 1 chiral center chiral or achiral molecule 3.2 How to draw tetrahedron

4) Enantiomers

2302169 Chem Med Studt


4.1 Labeling chiral centers with R or S (Cahn-Ingold-Prelog system) Assign a priority (1,2,3,4) to each group bonded to chiral center Use priority to label R or S isomer

STEREOCHEMISTRY

Priority Rule Rule 1: assign priorities (1,,4) to the atoms directly bonded to chiral center in order of decreasing atomic number
4 Atomic number: Br> Cl > F >H 3 2 H F C Br Cl 1

Rule 2: If two atoms on chiral center are identical, assign priority based on atomic number of the atoms bonded to these atoms. One atom of higher atomic number determines a higher priority

Rule 3: If two isotope are bonded to the chiral center,assign priorities in order of decreasing mass number.
4 1 Br H C Cl 2 D 3 heavier isotope

Rule 4: To assign a priority to an atom that is part of a multiple bond, treat a multiple bonded atom as an equivalent number of single bon atoms

Labeling R or S to Chiral Center Step 1: assign priorities from 1 to 4

2-butanol
1 OH 4 2 H C CH 2CH3 H 3C 3 A

1 OH Priority: -OH, -CH 2CH3, -CH 3, -H

4 C H 2 H 3CH 2C CH3 3 B

2302169 Chem Med Studt

STEREOCHEMISTRY

Step 2: orient the molecules with lowest priority (4) back and visual the remaining priorities (1-3)
1 OH Enantiomer A H C 3 H 3C 4 CH 2CH 3 2 eye 1 OH H 3C 3 CH 2CH3 2

1 OH Enantiomer B 4 C H 2 H 3 CH 2C CH 3 3 H 3CH 2C 2

1 OH CH 3 3

Step 3: Trace a circle from priority group 123


1 OH 3 H 3C CH 2CH 3 2 1 OH S-isomer 2 H 3 CH 2C CH 3 3 clockwise directiion R -isomer

Enantiomer A

counterclockwise directiion

Enantiomer B

5) Diastereomers 5.1 Configurational diastereomers


H 3CH2 C

* *

H H CH 3 Br Br chiral center, n = 2 max. stereoisomers = 4

2,3-dibromopentane

5.2 Cis-trans diastereomers


Alkene H3C H H CH 3 H3C H CH 3 H CH3 H H CH3 Cycloalkane CH3 H CH3 H

t rans -2-Butene

cis -2-Butene

t rans -1,3-dimethylcyclopentane

cis -1,3-dimethylcyclopentane

2302169 Chem Med Studt


6) Meso Compounds

STEREOCHEMISTRY

H 3C Br H C

CH 3 Br H

H 3C Br H D identical

CH 3 Br H

Isomers
diff erent compounds with the same molecular formula

Constitutional isomers
isomers having atoms bonded to diff erent atoms

Stereoisomers
isomers with a difference in 3D arrangement only

Enantiomers
mirror images

Diastereomers
not mirror images

Congifurational diastereomers

Cis-Trans diastereomers

7) Optical Activity of Stereoisomer

2302169 Chem Med Studt


7.1 Rotation of polarized light

STEREOCHEMISTRY

Achiral Molecule >> Optically Inactive

Chiral Molecule >> Optically Active

Two enantiomers: rotate plane-polarized light to an equal extent but in opposite directions. No relationship exists between R and S prefixes and the (+) and (-) designations that indicate optical rotation. 7.2 Specific rotation

7.3 Racemic mixture and enantiomeric excess (ee) : A mixture containing equal amount of two enantiomers. Denoted by the symbol ()

ee = % of one enantiomer - % of the other enantiomer ee = ([] mixture/[] pure enantiomer) x 100.

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