6 Stereochemistry

Chiral Molecules and their Properties

Stereochemistry

Stereochemistry

Stereochemistry
3
Isomer

Stereoisomer Isomer 3

Isomer
1. Conformational isomer Conformer

ethane
3

 Isomer()

2. Configurational isomer

Configurational isomer

Configurational isomer

Geometric Isomer
configurational isomer 2


C
isomer
optical isomer

Geometric Isomer ()

Geometric Isomer

90 p-orbital C

(Overlap)

Geometric Isomer ()
C-C
60 kcal/mole

20 kcal/mole
C-C

Geometric Isomer ()

2
C hybidization sp

C -

Geometric Isomer ()
2

Geometric Isomer ()

geometric
isomer ethylene
geometric isomer
geometric isomer
C

geometric isomer 2 isomer

 Geometric Isomer
4 C-C
2
2
cis-isomer
trans-isomer

 Geometric Isomer()

cis- trans- geometric isomer

geometric isomer

cis- trans- geometric isomer()

trans-geometric isomer
cisgeometric isomer trans-2-butane
cis-2-butane
1
geometric isomer 2,4-heptadiene
4 geometric isomer

cis- trans- geometric isomer()

geometric isomer
n optical
isomer geometric
n
isomer 2 isomer

 (E) (Z)

C

isomer E
( across)

isomer Z
( together)

Stereoisomer

Stereomer


Configurational isomer
2 1. enantiomer
2. diastereomer

1.Enantiomer

stereoisomer


(mirror image)
(nonsuperimposable)

Enantiomer()

3
sp

4
C
(asymmetric carbon)

Enantiomer ()

chiral carbon
enantiomer 2-butanol
trans-1,2-cyclohexanediol

Enantiomer ()

chiral carbon
asymmetric carbon
(plane of symmetry)


dichloromethane, cis-2-butene trans-2butene

Enantiomer ()

enantiomer

Enantiomer ()

enantiomer
4 chiral carbon

Enantiomer ()

chiral plane

chiral carbon
enantiomer
cumulene
2 isomer

Enantiomer ()

Enantiomer ()

isomer
isomer

Enantiomer ()

cumulene enantiomer

Enantiomer ()

plane of polarized light
optically active

plane of polarized light
optically inactive

2.Diastereomer

diastereoisomer stereomer



(non-superimposable)

Diastereomer ()

4

diastereomer
cis-2-butene trans-2-butene

Diastereomer ()

Diastereomer ()

2

diastereomer cyclohexane
1 4 cis-
trans- diastereomer
enantiomer

Diastereomer()

diastereomer
chiral carbon 2
enantiomer 2-3-pentanediol
chiral carbon 2 3
stereoisomer 4 isomer
enantiomer
diastereomer

Optical Activity

polarize polarimeter

monochromatic
light

Optical Activity
polarimeter polarizer
monochromatic light
monochromatic light
optically
active polarize
analyzer

Optical Activity ()

polarize
(specific rotation)

Optical Activity ()
Isomer

Isomer
Optical
Activity

Optical Activity ()

polarize
optical activity enantiomer
optical isomer
optical activity polarize
dextrorotatory isomer (+)
optical activity polarize
levorotatory isomer (-)

Racemic Mixture

enantiomer 50%

chiral atom
chiral atom
racemic mixture

Racemic Mixture

polarize
enantiomer
enantiomer racemic
Mixture Optical Activity

 Racemic Mixture

enantiomer Resolution

enantiomer
diastereoisomer

 Racemic Mixture
enantiomer racemic
mixture reagent
optical activity
diastereoisomer
racemic-1-phenylethylamine
lactic acid optical activity

 Racemic Mixture

diastereoisomer


diastereoisomer
hydroxide ion