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. Implicit in a mechanism is the stereochemistry of the reaction: in other words, the relative three-dimensional orientation of the reacting particles at any time in the reaction. Concentrating on organic chemistry, early chapters deal mainly with definitions of terms such as chirality, enantiomers, diastereoisomers and racemization, 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. Chirality without a stereogenic centre, in molecules such as allenes for example, is also covered. The distinction between conformation and configuration is developed to include assignment of configurations to di-substituted cyclohexanes and to the decalins. The conventions E, Z and Re, Si are introduced for sp2 hybridized carbons as found in alkenes and carbonyl compounds. Diastereotopic groups are discussed. 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. Additional material is available on the website at www.rsc.org/tct Ideal for the needs of undergraduate chemistry students, Tutorial Chemistry Texts is a major series consisting of short, single topic or modular texts concentrating on the fundamental areas of chemistry taught in undergraduate science courses. Each book provides a concise account of the basic principles underlying a given subject, embodying an independent-learning philosophy and including worked examples.
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achiral acid alcohol alkene alkyl allene anomeric effect anti Assign configuration axial axis biphenyls bond angles bridgehead carbons bromine bromonium ion C-H bonds carbon atoms carbon-carbon carbonyl carbonyl carbon carbonyl group chair conformation Chapter Chem Chemistry chiral chiral molecules clockwise CO2H compound convention cyclic cyclobutanes cyclohexane cyclopentanes cyclopropane diastereoisomers diastereomeric diastereotopic dihedral angle disubstituted double bond eclipsed electron enantiomerically pure enantiomers enantiotopic energy enzyme equatorial ester ethane ethene example face Figure Fischer projection give homotopic hydrogens hydroxyl identical interactions inversion of configuration ketone kJ mol leaving group LiAlH4 meso methyl groups mirror image molecular model molecule Newman projection nitrogen nomenclature nucleophile OH OH oxidation oxime oxygen pair plane of symmetry priority prochiral protons racemic rate constant reagent ring inversion ring junction rotation salts SN2 reaction stable stereo stereochemical stereochemistry stereogenic carbon stereogenic centres stereoisomers strain structure substituents tion trans