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Chapter 5 Stereoisomerism.docx

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Department
Chemistry
Course
CHEM 2OA3
Professor
Harald Stover
Semester
Fall

Description
1Chapter 5 StereoisomerismBernard HoOctober 25 201151 Overview of IsomerismIsomers are compounds that are constructed from same atoms but that still differ from each otherConstitutional isomers differ in connectivity of their atomsoAre thus different compounds with different physical properties Stereoisomers are compounds that have same constitution but differ in spatial arrangement of their atomsoEx cistrans stereoisomerism among substituted cycloalkanesoCan also describe cistrans in double bondsoThey represent two different compounds because double bond does not experience free rotation as single bonds doRecall thatbond is formed from overlap of two p orbitalsRotation about CC would effectively destroy overlap between p orbitalsIn order to use cistrans terminology to differentiate stereoisomers there must be two identical groups to compareHydrogen atoms can also be used to assign cistrans terminologyWhen two identical groups are connected to same position same carbon there cannot be cistrans isomerism because they represent same compound52 Introduction to StereoisomerismChiralityoObject that are not superimposable on their mirror images are called chiral objectsoAll 3D objects can be classified as either chiral or achiralChirality Centers
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