chapter3

chapter3 - 3-3-1Organic Organic ChemistryChemistryWilliam...

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Unformatted text preview: 3-3-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson3-3-2StereoisomerismStereoisomerismand Chiralityand ChiralityChapter 3Chapter 33-3-3IsomersIsomersIsomers:Isomers:different compounds with the same molecular formulaConstitutional isomers:Constitutional isomers:isomers with a different connectivityStereoisomers:Stereoisomers:isomers with the same connectivity but a different orientation of their atoms in space3-3-4ChiralityChiralityChiral:Chiral:from the Greek, cheir, handan object that is not superposable on its mirror imageAchiral:Achiral:an object that lacks chirality; one that lacks handednessan achiral object has at least one element of symmetryplane of symmetry:plane of symmetry:an imaginary plane passing through an object dividing it so that one half is the mirror image of the other halfcenter of symmetry:center of symmetry:a point so situated that identical components are located on opposite sides and equidistant from that point along the axis passing through it3-3-5Elements of SymmetryElements of SymmetrySymmetry in objectsSymmetry in objects3-3-6Elements of SymmetryElements of SymmetryPlane of symmetry (contd)HOOHmirrorplane3-3-7Chiral CenterChiral CenterThe most common (but not the only) cause of chirality in organic molecules is a tetrahedral atom, most commonly carbon, bonded to four different groupsA carbon with four different groups bonded to it is called a chiral centerchiral centerall chiral centers are stereocenters, but not all stereocenters are chiral centers (see Figure 3.5)Enantiomers:Enantiomers:stereoisomers that are nonsuperposable mirror imagesrefers to the relationship between pairs of objects3-3-8EnantiomersEnantiomers2-Butanolhas one chiral centerhere are four different representations for one enantiomerusing (4) as a model, here are two different representations for the enantiomer of (4)OHCH3CCH2CH3HOHCH3CCH2CH3HHOHOH(1)(2)(3)(4)OH(4)OHOHrepresentations for theenantiomer of (4)3-3-9EnantiomersEnantiomersThe enantiomers of lactic aciddrawn in two different representationsCCHOCH3HOHOCCOHCH3HOOHOHOHOOHHOO3-3-1010EnantiomersEnantiomers2-ChlorobutaneCH3CHCH2CH3ClClHClH3-3-1111EnantiomersEnantiomers3-ChlorocyclohexeneClCl3-3-1212EnantiomersEnantiomersA nitrogen chiral centerNCH2CH3H3CNCH3CH3CH2A pair of enantiomers++3-3-1313R,SR,SConventionConventionPriority rules1. Each atom bonded to the chiral center is assigned a priority based on atomic number; the higher the atomic number, the higher the priority2. If priority cannot be assigned per the atoms bonded to the chiral center, look to the next set of atoms; priority is assigned at the first point of difference(53)(35)(17)(16)(8)(7)(6)(1)Increasing priority- H -CH3 -NH2 - OH - SH - Cl - Br - IIncreasing priority(8)(7)(6)(1)-CH2-OH- CH2-NH2- CH2-CH3-CH2-H3-...
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chapter3 - 3-3-1Organic Organic ChemistryChemistryWilliam...

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