Chirality. Chapter 5 Stereochemistry. Chiral Carbons. Stereoisomers. Mirror Planes of Symmetry. (R), (S) Nomenclature

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1 Organic hemistry, 5 th Edition L. G. Wade, Jr. hapter 5 Stereochemistry hirality andedness : right glove doesn t fit the left hand. Mirror-image object is different from the original object. Jo Blackburn Richland ollege, Dallas, TX Dallas ounty ommunity ollege District 2003, Prentice all hapter 5 2 Stereoisomers Geometric isomers: cis-trans isomers. Enantiomers: nonsuperimposable mirror images, different molecules. l l l l cis-1,2-dichlorocyclopentane l l l l trans -1,2-dichlorocyclopentane hapter 5 3 hiral arbons Tetrahedral carbons with 4 different attached groups are chiral. Its mirror image will be a different compound (enantiomer). hapter 5 4 Mirror Planes of Symmetry If two groups are the same, carbon is achiral. (animation) A molecule with an internal mirror plane cannot be chiral. aution! If there is no plane of symmetry, molecule may be chiral or achiral. See if mirror image can be superimposed. hapter 5 5 (R), (S) Nomenclature Different molecules (enantiomers) must have different names. Usually only one enantiomer will be biologically active. onfiguration around the chiral carbon is specified with (R) and (S). O O 3 hapter 5 6 N 2 natural alanine 1

2 ahn-ingold-prelog Rules Assign a priority number to each group attached to the chiral carbon. Atom with highest atomic number assigned the highest priority #1. In case of ties, look at the next atoms along the chain. Double and triple bonds are treated like bonds to duplicate atoms. hapter 5 7 O 2 O N 2 natural alanine Assign Priorities 3 2 expands to 4 ( 3 ) O O 2 4 l 3 2 l 1 2 O ( 3 ) 2 2 O O hapter 5 8 Assign (R) or (S) Working in 3D, rotate molecule so that lowest priority group is in back. Draw an arrow from highest to lowest priority group. lockwise = (R), ounterclockwise = (S) Properties of Enantiomers Same boiling point, melting point, density Same refractive index Different direction of rotation in polarimeter Different interaction with other chiral molecules Enzymes Taste buds, scent hapter 5 9 hapter 5 10 Optical Activity Rotation of plane-polarized light Enantiomers rotate light in opposite directions, but same number of degrees. Polarimetry Use monochromatic light, usually sodium D Movable polarizing filter to measure angle lockwise = dextrorotatory = d or (+) ounterclockwise = levorotatory = l or (-) Notrelated to (R) and (S) hapter 5 11 hapter

3 Specific Rotation Observed rotation depends on the length of the cell and concentration, as well as the strength of optical activity, temperature, and wavelength of light. [α] = α (observed) c l alculate [α] D A 1.00-g sample is dissolved in 20.0 ml ethanol ml of this solution is placed in a 20.0-cm polarimeter tube at 25. The observed rotation is 1.25 counterclockwise. c is concentration in g/ml l is length of path in decimeters. hapter 5 13 hapter 5 14 Biological Discrimination Racemic Mixtures Equal quantities of d- and l- enantiomers. Notation: (d,l) or (±) No optical activity. The mixture may have different b.p. and m.p. from the enantiomers! hapter 5 15 hapter 5 16 Racemic Products If optically inactive reagents combine to form a chiral molecule, a racemic mixture of enantiomers is formed. hapter 5 17 Optical Purity Also called enantiomeric excess. Amount of pure enantiomer in excess of the racemic mixture. If o.p. = 50%, then the observed rotation will be only 50% of the rotation of the pure enantiomer. Mixture composition would be hapter

4 alculate % omposition The specific rotation of (S)-2-iodobutane is Determine the % composition of a mixture of (R)- and (S)-2-iodobutane if the specific rotation of the mixture is hirality of onformers If equilibrium exists between two chiral conformers, molecule is not chiral. Judge chirality by looking at the most symmetrical conformer. yclohexane can be considered to be planar, on average. hapter 5 19 hapter 5 20 Mobile onformers Nonsuperimposable mirror images, but equal energy and interconvertible. Use planar approximation. Nonmobile onformers If the conformer is sterically hindered, it may exist as enantiomers. hapter 5 21 hapter 5 22 Allenes hiral compounds with no chiral carbon ontains sp hybridized carbon with adjacent double bonds: -==- End carbons must have different groups. Fischer Projections Flat drawing that represents a 3D molecule A chiral carbon is at the intersection of horizontal and vertical lines. orizontal lines are forward, out-of-plane. Vertical lines are behind the plane. Allene is achiral. hapter 5 23 hapter

5 Fischer Rules arbon chain is on the vertical line. ighest oxidized carbon at top. Rotation of 180 in plane doesn t change molecule. Do not rotate 90! Do not turn over out of plane! Fischer Mirror Images Easy to draw, easy to find enantiomers, easy to find internal mirror planes. Examples: 3 l l 3 l 3 l 3 3 l l 3 hapter 5 25 hapter 5 26 Fischer (R) and (S) Lowest priority (usually ) comes forward, so assignment rules are backwards! lockwise is (S) and counterclockwise is (R). Example: (S) 3 l l (S) 3 Diastereomers Stereoisomers that are not mirror images. Geometric isomers (cis-trans) Molecules with 2 or more chiral carbons. hapter 5 27 hapter 5 28 Alkenes is-trans isomers are not mirror images, so these are diastereomers. 3 3 cis-2-butene 3 3 trans-2-butene hapter 5 29 Ring ompounds is-trans isomers possible. May also have enantiomers. Example: trans-1,3-dimethylcylohexane hapter

6 Two or More hiral arbons Enantiomer? Diastereomer? Meso? Assign (R) or (S) to each chiral carbon. Enantiomers have opposite configurations at each corresponding chiral carbon. Diastereomers have some matching, some opposite configurations. Meso compounds have internal mirror plane. Maximum number is 2 n, where n = the number of chiral carbons. hapter 5 31 Examples OO OO O O O O OO OO (2R,3R)-tartaric acid (2S,3S)-tartaric acid OO O O OO (2R,3S)-tartaric acid hapter 5 32 Fischer-Rosanoff onvention Before 1951, only relative configurations could be known. Sugars and amino acids with same relative configuration as (+)-glyceraldehyde were assigned D and same as (-)-glyceraldehyde were assigned L. With X-ray crystallography, now know absolute configurations: D is (R) and L is (S). No relationship to dextro- or levorotatory. hapter 5 33 D and L Assignments O O 2 O D-(+)-glyceraldehyde OO 2 N 2 2 OO L-(+)-glutamic acid O O O O O 2 O D-(+)-glucose hapter 5 34 Properties of Diastereomers Diastereomers have different physical properties: m.p., b.p. They can be separated easily. Enantiomers differ only in reaction with other chiral molecules and the direction in which polarized light is rotated. Enantiomers are difficult to separate. hapter 5 35 Resolution of Enantiomers React a racemic mixture with a chiral compound to form diastereomers, which can be separated. hapter

7 hromatographic Resolution of Enantiomers End of hapter 5 hapter 5 37 hapter

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