Organic Chemistry

Organic Chemistry - Ch 11 566 Daley & Daley••43 SCH 3 OCH 3 CH 212(S)-Ethyl methyl sulfoxideExercise 11.10What is the isomeric relationship between the two forms of thefollowing compound that are interconverted by amine inversion?Could you isolate this compound in an optically active form?CH 3H••C N CH3C N CH 3CH ••CH 3 CH 32CH 2 CH 3HCH 3 CH 2CH 2 CH 3Key Ideas from Chapter 11❏ All three-dimensional objects are either symmetric orasymmetric. You can superimpose a symmetric object onto itsmirror image, but you cannot superimpose an asymmetricobject onto its mirror image.❏❏Stereoisomers are molecules that have the same sequence ofbonds, but have a different arrangement of the atoms in space.There are two types of stereoisomers.1. Enantiomers: Compounds that have a mirror imagerelationship.2. Diastereomers: Stereoisomers that are not enantiomers.❏A carbon atom bonded to four different groups is stereogeniccenter. A molecule with a single stereogenic center isasymmetric. Molecules with more than one stereocenter may bechiral molecules or they may be meso molecules. Mesomolecules are symmetrical molecules with even numbers ofstereogenic center. Meso isomers occur with molecules thathave an internal plane of symmetry.www.ochem4free.com 5 July 2005