Simple molecules: hybridization, conformation aand configuration -- Chiral molecules: one stereogenic centre -- Molecules with two (or more) stereogenic centres -- Stereochemistry of carbon-carbon and carbon-nitrogen double bonds -- Chirality without stereogenic carbon -- Stereoisomerism in cyclic structures -- Substitution reactions at saturated carbon -- Prochirality, enantiotopic and diastereotopic groups and faces: use of nmr spectroscopy in stereochemistry -- Answers to problems.
Summary:
Stereochemistry is defined as the study of the three-dimensional structure of molecules. Stereochemical considerations are important in both isomerism and studies of the mechanisms of chemical reactions. Concentrating on organic chemistry, early chapters deal mainly with definitions of terms such as chirality, enantiomers, diastereoisomers and racemisation, complete with suitable examples to illustrate key concepts. Use of a polarimeter and associated definitions are described, together with two different conventions D, L and R, S for specification of configuration. The distinction between conformation and configuration is developed to include assignment onf configurations to di-substituted cyclohexanes and to the decalins. Aspects of stereochemistry are explored through consideration of addition reactions to alkenes and carbonyl groups, nucleophilic substitution, and reactions (and interactions) involved in the resolution of racemic mixtures.
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