Chapter 7 Stereochemistry. 7.1 Molecular Chirality: Enantiomers.

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Presentation transcript:

Chapter 7 Stereochemistry

7.1 Molecular Chirality: Enantiomers

A molecule is chiral if its two mirror image forms are not superposable upon one another. A molecule is achiral if its two mirror image forms are superposable. Chirality

Br Cl H F Bromochlorofluoromethane is chiral It cannot be superposed point for point on its mirror image.

Br Cl H F Bromochlorofluoromethane is chiral H Cl Br F To show nonsuperposability, rotate this model 180° around a vertical axis.

Br Cl H F Bromochlorofluoromethane is chiral H Cl Br F

Another look

are enantiomers with respect to each other and nonsuperposable mirror images are called enantiomers Enantiomers

Isomers stereoisomers constitutionalisomers

Isomers stereoisomers constitutionalisomers diastereomers enantiomers

Chlorodifluoromethane is achiral

The two structures are mirror images, but are not enantiomers, because they can be superposed on each other.

7.2 The Stereogenic Center

a carbon atom with four different groups attached to it also called: chiral center asymmetric center stereocenter The Stereogenic Center wx y z C

A molecule with a single stereogenic center is chiral. Bromochlorofluoromethane is an example. Chirality and stereogenic centers Cl F Br H C

A molecule with a single stereogenic center is chiral. 2-Butanol is another example. Chirality and stereogenic centers CH 3 OH H C CH 2 CH 3

Examples of molecules with 1 stereogenic center CH 3 C CH 2 CH 3 CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 a chiral alkane

Examples of molecules with 1 stereogenic center Linalool, a naturally occurring chiral alcohol OH

Examples of molecules with 1 stereogenic center 1,2-Epoxypropane: a stereogenic center can be part of a ring O H2CH2CH2CH2C CHCH 3 attached to the stereogenic center are: —H —CH 3 —OCH 2 —CH 2 O

Examples of molecules with 1 stereogenic center Limonene: a stereogenic center can be part of a ring CH 3 H C CH 2 attached to the stereogenic center are: —H —CH 2 CH 2 —CH 2 CH= —C=

Examples of molecules with 1 stereogenic center Chiral as a result of isotopic substitution CH 3 C D TH

A molecule with a single stereogenic center must be chiral. But, a molecule with two or more stereogenic centers may be chiral or it may not (Sections ).

7.3 Symmetry in Achiral Structures

Symmetry tests for achiral structures Any molecule with a plane of symmetry or a center of symmetry must be achiral.

A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry. Plane of symmetry

A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry. Plane of symmetry

A plane of symmetry bisects a molecule into two mirror image halves. 1-Bromo-1-chloro-2-fluoroethene has a plane of symmetry. Plane of symmetry

A plane of symmetry bisects a molecule into two mirror image halves. 1-Bromo-1-chloro-2-fluoroethene has a plane of symmetry. Plane of symmetry

A point in the center of the molecule is a center of symmetry if a line drawn from it to some element, when extended an equal distance in the opposite direction, encounters an identical element. Center of symmetry

A point in the center of the molecule is a center of symmetry if a line drawn from it to any element, when extended an equal distance in the opposite direction, encounters an identical element. Center of symmetry