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  Other Configurational Notations Homework Help - K-12 Grade Level, College Level Chemistry

Introduction to Other Configuration Notations

Fischer projection formulas are mainly helpful for comparing configurational isomers in a family of related chiral compounds, like the carbohydrates. Though, the eclipsed conformations understood by these representations are unrealistic. When explaining acyclic compounds incorporating two or more chiral centers, for the primary carbon chain several chemists desire to write zig-zag line formulas. Here, in a plane, the zig-zag carbon chain lies and the relative or absolute configurations at the chiral centers are then entitled hatched or wedge bonds to substituent groups. This is demonstrated for D-(-)-ribose and the diastereoisomeric D-tetroses erythrose and threose in the picture.

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These compounds are all chiral and only one enantiomer is drawn (the D-family member). Again and again, though, we must consider and name diastereoisomers which are achiral or racemic. For  an instance, addition of chlorine to cis-2-butene yields a stereoisomer of 2,3-dichlorobutane distinct from the one got by chlorine addition to trans-2-butene. In cases that are having two adjacent chiral centers, like this, the prefixes threo and erythro may be used to entitle the relative configuration of the centers. These prefixes, taken out from the names of the tetroses threose and erythrose, may be useful to racemic compounds, similarly pure meso compounds and enantiomers, as displayed in the diagram. In the generally employed zig-zag drawings substituents may lie on similar side of the carbon chain, a syn orientation or on opposite sides, an anti orientation. In a Fischer formula for adjacent substituents this is opposite to their location. So, the substituents in the erythro isomer have an anti orientation, but are syn in the threo isomer.

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The syn-anti nomenclature can be applied to acyclic compounds that are having more than two chiral centers, as demonstrated by the example in the colored box. The stereogenic center nearest carbon no.1 serves as a reference. At sites having two substituents, like carbon no.5, the terms refer to the relative orientation of the highest order substituent, as depicted by the C.I.P. sequence rules.

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