有机化学英文课件hapter3.pptVIP

Organic Chemistry William H. Brown Christopher S. Foote Brent L. Iverson Isomers Isomers: different compounds with the same molecular formula Constitutional isomers: isomers with a different connectivity Stereoisomers: isomers with the same connectivity but a 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 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 objects Elements of Symmetry Plane of symmetry (cont’d) 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 chiral 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 enantiomer using (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 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