Lecture_10.pdf - C10J – Organic Chemistry Lecture 10 Stereoisomerism Chirality The(R-S System of Nomenclature Chirality Any two objects that bear a

Lecture_10.pdf - C10J – Organic Chemistry Lecture 10...

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C10J – Organic Chemistry Lecture 10
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Stereoisomerism checkbld Chirality checkbld The ( R-S ) System of Nomenclature
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Chirality Any two objects that bear a similar relationship to each other as your right hand does to your left hand, are described as being chiral . Your right and left hands are non-superposable mirror images of each other. Chiral objects are said to exhibit chirality .
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Chirality Chirality is also observed at the level of molecules. Consider a molecule in which a tetrahedral carbon (sp 3 hybridized) is bonded to four different groups.
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C Tetrahedral carbon bonded to four different groups
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Compounds, A and B are Chiral Molecules ( They Exist as Non-Superposable Mirror Images ) C Mirror plane C C A B C Compounds A and B are not superposable Compounds A and B represent two different Molecules.
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Chiral Molecules A molecule and its mirror image represent two different chemical entities. A molecule and its mirror image have the same molecular formula, the same connectivity of atoms but differ in the way in which the atoms are arranged in space. They are Stereoisomers .
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Chiral Molecules C C C C Mirror plane A B Compounds A and B are not superposable Nonsuperposable mirror images are called Enantiomers. A and B are enantiomers.
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Isomerism ISOMERS Consititutional isomers Enantiomers Stereoisomers Diastereomers (Nonsuperposable mirror images) (Stereoisomers that are not mirror images eg. cis and trans isomers of alkenes)
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Stereoisomerism Key Words • Chiral • Achiral ( this means not chiral) • Enantiomers • Diastereomers Racemic mixture Stereocentre / Asymmetric carbon
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Enantiomers C C A B Asymmetric carbon or Stereocentre Mirror plane C CH 3 CH 2 H NH 2 CH 3 C CH 2 CH 3 H N H 2 C H 3 Nonsuperposable mirror images of 2-aminobutane
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Enantiomers Cont’d C C Mirror plane A B C F H Br Cl C F H Br Cl Nonsuperposable mirror images of bromochlorofluoromethane
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