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1、Organic Chemistry,William H. Brown Christopher S. Foote Brent L. Iverson,Stereoisomerism and Chirality,Chapter 3,Isomers,Isomers: different compounds with the same molecular formula Constitutional isomers: isomers with a different connectivity Stereoisomers: isomers with the same connectivity but a
2、different orientation of their atoms in space,Chirality,Chiral: from the Greek, cheir, hand an object that is not superposable on its mirror image Achiral: an object that lacks chirality; one that lacks handedness an achiral object has at least one element of symmetry plane of symmetry: an imaginary
3、 plane passing through an object dividing it so that one half is the mirror image of the other half 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,Elements of Symmetry,Symmetry in objec
4、ts,Elements of Symmetry,Plane of symmetry (contd),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 all chira
5、l centers are stereocenters, but not all stereocenters are chiral centers (see Figure 3.5) Enantiomers: stereoisomers that are nonsuperposable mirror images refers to the relationship between pairs of objects,Enantiomers,2-Butanol has one chiral center here are four different representations for one
6、 enantiomerusing (4) as a model, here are two different representations for the enantiomer of (4),Enantiomers,The enantiomers of lactic acid drawn in two different representations,Enantiomers,2-Chlorobutane,Enantiomers,3-Chlorocyclohexene,Enantiomers,A nitrogen chiral center,R,S Convention,Priority
7、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 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 di
8、fference,R,S Convention,3. Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of similar atoms by single bonds,Naming Chiral Centers,1. Locate the chiral center, identify its four substituents, and assign priority from 1 (highest) to 4 (lowest) to each
9、 substituent 2. Orient the molecule so that the group of lowest priority (4) is directed away from you 3. Read the three groups projecting toward you in order from highest (1) to lowest priority (3) 4. If the groups are read clockwise, the configuration is R; if they are read counterclockwise, the c
10、onfiguration is S(S)-2-Chlorobutane,Naming Chiral Centers,(R)-3-Chlorocyclohexene(R)-Mevalonic acid,Enantiomers & Diastereomers,For a molecule with 1 chiral center, 21 = 2 stereoisomers are possible For a molecule with 2 chiral centers, a maximum of 22 = 4 stereoisomers are possible For a molecule w
11、ith n chiral centers, a maximum of 2n stereoisomers are possible,Enantiomers & Diastereomers,2,3,4-Trihydroxybutanal two chiral centers22 = 4 stereoisomers exist; two pairs of enantiomersDiastereomers: stereoisomers that are not mirror images refers to the relationship among two or more objects,Enan
12、tiomers & Diastereomers,2,3-Dihydroxybutanedioic acid (tartaric acid) two chiral centers; 2n = 4, but only three stereoisomers existMeso compound: an achiral compound possessing two or more chiral centers that also has chiral isomers,Enantiomers & Diastereomers,2-Methylcyclopentanol,Enantiomers & Di
13、astereomers,1,2-Cyclopentanediol,H,H,H,H,H,H,H,H,diastereomers,Enantiomers & Diastereomers,cis-3-Methylcyclohexanol,Enantiomers & Diastereomers,trans-3-Methylcyclohexanol,Isomers,Properties of Stereoisomers,Enantiomers have identical physical and chemical properties in achiral environments Diastereo
14、mers are different compounds and have different physical and chemical properties meso tartaric acid, for example, has different physical and chemical properties from its enantiomers (see Table 3.1),Plane-Polarized Light,Ordinary light: light vibrating in all planes perpendicular to its direction of
15、propagation Plane-polarized light: light vibrating only in parallel planes Optically active: refers to a compound that rotates the plane of plane-polarized light,Plane-Polarized Light,plane-polarized light is the vector sum of left and right circularly polarized light circularly polarized light reac
16、ts one way with an R chiral center, and the opposite way with its enantiomer the result of interaction of plane-polarized light with a chiral compound is rotation of the plane of polarization,Plane-Polarized Light,Polarimeter: a device for measuring the extent of rotation of plane-polarized light,Op
17、tical Activity,observed rotation: the number of degrees, , through which a compound rotates the plane of polarized light dextrorotatory (+): refers to a compound that rotates the plane of polarized light to the right levorotatory (-): refers to a compound that rotates of the plane of polarized light to the left specific rotation: observed rotation when a pure sample is placed in a tube 1.0 dm in length and concentration in g/mL (density); for a solution, concentration is expressed in g/ 100 mL,
