Lecture 8: September 13, 2012
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1 CHM 223 Organic Chemistry I Fall 2012, Des Plaines Prof. Chad Landrie Lecture 8: September 13, 2012 Skillbuilder 2 Ch. 5: Stereochemistry (Sec8ons )
2 CHM 223 Organic Chemistry I Fall 2012, Des Plaines Prof. Chad Landrie Ch. 5: Stereochemistry SecHons
3 CHM 223 Organic Chemistry I Fall 2012, Des Plaines Prof. Chad Landrie (S)-Carvone (R)-Carvone Stereoisomers Chapter 5: SecHons
4 Chirality HO Cl CH 3 CH 3 Cl OH mirror image 180 º Cl HO CH A molecule is chiral if its two mirror image forms are not superimposable on one another Superimposable molecules can be laid on top of one another so that all equivalent atoms (points) line up Slide 4
5 Chiral Objects chiral: non-superimposable mirror images snail mirror image Slide 5
6 Chiral Objects chiral: non-superimposible mirror images milkyway mirror image Slide 6
7 Chirality chiral: non-superimposible mirror images hair whorl mirror image Slide 7
8 Chirality chiral: non-superimposible mirror images fingerprint mirror image Slide 8
9 Chirality chiral: non-superimposible mirror images DNA double helix mirror image Slide 9
10 Chirality chiral: non-superimposable mirror images cheir (Greek) = hand chirality is synonymous with handedness Slide 10
11 Molecules can Also Be Chiral chiral: non-superimposible mirror images Br Cl H H Cl Br F F Slide 11
12 Superimposibility To check for superimposibility, rotate mirror image 180º along a plane perpendicular to the mirror plane 180º Br Cl H H Cl Br F F Slide 12
13 Non- superimposible if the images chiral: are not non-superimposible identical, they are non mirror superimposible; images not all points (atoms) line up Br Cl F H Cl Br F H Slide 13
14 Not Everything is Chiral! achiral: not chiral; mirror images are superimposible basketball mirror image Slide 14
15 Not Everything is Chiral! achiral: not chiral; mirror images are superimposible Slide 15
16 Not Everything is Chiral! achiral: not chiral; mirror images are superimposible Slide 16
17 Symmetry Tests for Achiral Molecules Any molecule with a plane of symmetry or a center of symmetry is achiral (not chiral) A plane of symmetry bisects a molecule into two mirror image halves Slide 17
18 Symmetry Tests for Achiral Molecules Any molecule with a plane of symmetry or a center of symmetry is achiral (not chiral) plane of symmetry H 3 C CH 3 A plane of symmetry bisects a molecule into two mirror image halves Slide 18
19 Symmetry Tests for Achiral Molecules Any molecule with a plane of symmetry or a center of symmetry is achiral (not chiral) Br plane of symmetry Cl A plane of symmetry bisects a molecule into two mirror image halves Slide 19
20 Symmetry Tests for Achiral Molecules Any molecule with a plane of symmetry or a center of symmetry is achiral (not chiral) plane of symmetry Br H C C Cl H A plane of symmetry bisects a molecule into two mirror image halves Slide 20
21 Symmetry Tests for Achiral Molecules Any molecule with a plane of symmetry or a center of symmetry is achiral (not chiral) center of symmetry: a line drawn from center of molecule to an element extends in opposite direction to an identical element Slide 21
22 Symmetry Tests for Achiral Molecules Any molecule with a plane of symmetry or a center of symmetry is achiral (not chiral) center of symmetry: a line drawn from center of molecule to an element extends in opposite direction to an identical element Slide 22
23 Chirality Center Chirality center: an atom bonded to ligands in a spatial arrangement which is not superimposable on its mirror image Asymmetric carbon: a carbon atom bonded to four different atoms or groups (a type of chirality center) Y W C Z X other terminology commonly used: stereocenter stereogenic center Do not use these terms to mean chirality center. They have a different meaning. Leroy G. Wage, J. J. Chem. Educ. 2006, 83, Mislow, K.; Siegel, J. J. Am. Chem. Soc. 1984, 106, Slide 23
24 Chirality Center A molecule with a single chirality center is chiral Br F C H bromochlorofluoromethane is chiral Cl Slide 24
25 Chirality Center A molecule with a single chirality center is chiral OH H 3 C C H CH 2 CH 3 2-butanol is chiral although two carbon atoms are bonded to the chirality center, they are part of different groups Slide 25
26 Chirality Center A molecule with a single chirality center is chiral H 2 C C O CH 3 1,2-epoxypropane: a chirality center can be part of a ring attached to the chirality center are: H -H -CH3 -CH2O -OCH2 Slide 26
27 Chirality Center A molecule with a single chirality center is chiral H chiral as a result of isotopic D C CH 3 substitution T Slide 27
28 1 Chirality Center = Chiral A molecule with a single chirality center must be chiral. But a molecule with two or more chirality centers may be chiral or it may not be chiral (Section 5.7) H 2 C C O CH 3 H F Br C Cl H OH H 3 C C H CH 2 CH 3 CH 3 Cl OH H D C CH 3 T Slide 28
29 Chirality Centers Other Than Carbon Since nitrogen undergoes rapid pyramidal inversion, it is not considered a chirality center. The energy barrier to inversion is large enough for phosphines and sulfoxides, that they are considered chirality centers. Ea (phospine) ~ 132 kcal/mol Ea (sulfoxide) ~ 45 kcal/mol Ea (amines) ~ 24 kcal/mol Slide 29
30 Chirality Centers Other Than Carbon Since nitrogen undergoes rapid pyramidal inversion, it is not considered a chirality center. The energy barrier to inversion is large enough for phosphines and sulfoxides, that they are considered chirality centers. Ea (phospine) ~ 132 kcal/mol Ea (sulfoxide) ~ 45 kcal/mol Ea (amines) ~ 24 kcal/mol Slide 30
31 Chirality Centers Other Than Carbon Since nitrogen undergoes rapid pyramidal inversion, it is not considered a chirality center. The energy barrier to inversion is large enough for phosphines and sulfoxides, that they are considered chirality centers. Ea (phospine) ~ 132 kcal/mol Ea (sulfoxide) ~ 45 kcal/mol Ea (amines) ~ 24 kcal/mol Slide 31
32 CHM 223 Organic Chemistry I Fall 2012, Des Plaines Prof. Chad Landrie CIP R- S NotaHon for Chirality Centers (aka: Sequence Rules) SecHon: 5.5
33 CIP R/S NotaGon Step One: Locate chirality center chirality center CH 3 HO Cl C H Slide 33
34 CIP R/S NotaGon Step Two: Orient molecule so that lowest ranked (CIP priority) atom or group points away from you chirality center CH 3 CH 3 H HO C C H Cl HO Cl Slide 34
35 CIP R/S NotaGon Step Three: Number 3 highest priority groups in order of decreasing priority (CIP sequence rules: higher molar mass of connected atom = higher priority) chirality center CH 3 3 CH 3 H HO C H 2 C 1 Cl HO Cl Slide 35
36 CIP R/S NotaGon Step Four: Determine rotation direction of groups in decreasing priority chirality center CH 3 3 CH 3 H HO Cl C H 2 HO C Cl 1 (R)-1-chloroethanol clockwise (rectus) = R counterclockwise (sinister) = S Slide 36
37 EnanGomers Molecules which are non-superimposible mirror images are called enantiomers. Enantiomer describes a relationship between two molecules (enantiomer: opposite handedness). OH enantiomers OH 180 º OH (S)-2-butanol (R)-2-butanol enantiomers have opposite configurations (R/S) at every chirality center Slide 37
38 Isomers isomers constitutional (structural) Do the molecules have the same connectivity? no yes stereoisomers Can the molecules be interconverted by rotation around single bonds? yes no conformational configurational Slide 38
39 Stereoisomers configurational stereoisomers geometrical Is the isomerism at a doulbe bond? yes no optical Are the compounds nonsuperimposible mirror images? yes no enantiomers diastereomers Slide 39
40 Stereogenic Center vs. Chirality Center A stereogenic center (stereocenter) is an atom bearing several groups that when two groups are interchanged, a stereoisomer is formed. Chirality center?: YES Stereogenic center?: YES Is chiral: nonsuperimposible mirror image no plane of symmetry S Is a stereogenic center: exchange of two groups gives stereoisomer Leroy G. Wage, J. J. Chem. Educ. 2006, 83, Mislow, K.; Siegel, J. J. Am. Chem. Soc. 1984, 106, R Slide 40
41 Stereogenic Center vs. Chirality Center A stereogenic center (stereocenter) is an atom bearing several groups that when two groups are interchanged, a stereoisomer is formed. Chirality center?: NO Stereogenic center?: YES Not chiral: superimposible mirror image plane of symmetry Cis Is a stereogenic center: exchange of two groups gives stereoisomer Not all stereogenic centers are chirality centers! Trans Leroy G. Wage, J. J. Chem. Educ. 2006, 83, Mislow, K.; Siegel, J. J. Am. Chem. Soc. 1984, 106, Slide 41
42 Stereogenic Center vs. Chirality Center A stereogenic center (stereocenter) is an atom bearing several groups that when two groups are interchanged, a stereoisomer is formed. Chirality center?: NO Stereogenic center?: YES Not chiral: superimposible mirror image plane of symmetry Z Is a stereogenic center: exchange of two groups gives stereoisomer Not all stereogenic centers are chirality centers! E Leroy G. Wage, J. J. Chem. Educ. 2006, 83, Mislow, K.; Siegel, J. J. Am. Chem. Soc. 1984, 106, Slide 42
43 CHM 223 Organic Chemistry I Fall 2012, Des Plaines Prof. Chad Landrie Next Lecture... Sections 5.3, 5.4, Bring your model sets!!
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