Stereochemistry.ppt

Stereochemistry The study of the three dimensional structure of molecules. Isomers—A review Constitutional/Structural Isomers: differ in their bonding sequence; their atoms are connected differently. Stereoisomers: have the same bonding sequence, but differ in the orientation of their atoms in space. One special type of stereoisomerism that you have seen is geometric isomerism (e.g. cis/trans isomers). Chirality Chiral: a chiral object is one that has right and left handed forms, or a nonsuperimposable (nonidentical) mirror image. A chiral object has a mirror image that is different from the original object. An object that is not chiral is described as “achiral”. An atom is chiral only if it has four different groups attached to it. The mirror image of a chiral molecule is called its enantiomer. Chiral Molecules vs. Chiral Centers A molecule with one chiral center is a chiral molecule. A molecule with more than one chiral center is achiral if it has a plane of symmetry. Enantiomers have identical physical properties (e.g. bp, mp, density) except that they rotate plane polarized light in equal but opposite directions. They are said to possess “optical activity” or to be “optically active”. Achiral molecules are not optically active! Optical Activity Optical Activity is measured with a polarimeter. A compound in a polarimeter can rotate plane polarized light to the right or left by a specific number of degrees that must be determined experimentally. Compounds that rotate plane polarized light to the right (clockwise) are called dextrorotatory (d), and compounds that rotate plane polarized light to the left (counter-clockwise) are called levorotatory (l). In IUPAC notation, this is abbreviated by the signs (+) and (-) respectively. Nomenclature of Chiral Carbon Atoms Cahn-Ingold-Prelog Rules: Assign a priority to each group bonded to the chiral carbon. The higher the atomic number of the atom, the higher its priority. With different isotopes of the same element, the