chapter3 - Organic Chemistry William H Brown Christopher S...

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3- 3-1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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3- 3-2 Stereoisomerism Stereoisomerism and Chirality and Chirality Chapter 3 Chapter 3
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3- 3-3 Isomers Isomers Isomers: Isomers: different compounds with the same molecular formula Constitutional isomers: Constitutional isomers: isomers with a different connectivity Stereoisomers: Stereoisomers: isomers with the same connectivity but a different orientation of their atoms in space
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3- 3-4 Chirality Chirality Chiral: Chiral: from the Greek, cheir , hand an object that is not superposable on its mirror image Achiral: Achiral: an object that lacks chirality; one that lacks handedness an achiral object has at least one element of symmetry plane 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 half center 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 it
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3- 3-5 Elements of Symmetry Elements of Symmetry Symmetry in objects Symmetry in objects
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3- 3-6 Elements of Symmetry Elements of Symmetry Plane of symmetry (cont’d) HO OH mirror plane
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3- 3-7 Chiral Center Chiral Center The most common (but not the only) cause of chirality in organic molecules is a tetrahedral atom, most commonly carbon, bonded to four different groups A carbon with four different groups bonded to it is called a chiral center chiral center all chiral centers are stereocenters, but not all stereocenters are chiral centers (see Figure 3.5) Enantiomers: Enantiomers: stereoisomers that are nonsuperposable mirror images refers to the relationship between pairs of objects
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3- 3-8 Enantiomers Enantiomers 2-Butanol has one chiral center here are four different representations for one enantiomer using (4) as a model, here are two different representations for the enantiomer of (4) OH C H 3 C CH 2 CH 3 H OH C H 3 C CH 2 CH 3 H H OH OH (1) (2) (3) (4) OH (4) OH OH representations for the enantiomer of (4)
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3- 3-9 Enantiomers Enantiomers The enantiomers of lactic acid drawn in two different representations C C HO CH 3 H O HO C C OH CH 3 H O OH OH OH O OH HO O
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3- 10 10 Enantiomers Enantiomers 2-Chlorobutane CH 3 CHCH 2 CH 3 Cl Cl H Cl H
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3- 11 11 Enantiomers Enantiomers 3-Chlorocyclohexene Cl Cl
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3- 12 12 Enantiomers Enantiomers A nitrogen chiral center N CH 2 CH 3 H 3 C N CH 3 CH 3 CH 2 A pair of enantiomers + +
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3- 13 13 R,S R,S Convention Convention Priority rules 1. Each atom bonded to the chiral center is assigned a priority based on atomic number; the higher the atomic number, the higher the priority 2. 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      -CH
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