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Exercise · Q23

Q.Distinguish between the R/SR/S (CIP) system and the D/LD/L (relative) system for describing the configuration at a stereocentre. Which system is based purely on atomic-number priorities, and which is based on comparison with a reference compound?

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The R/SR/S (CIP) system assigns a configuration by ranking the four substituents at a stereocentre purely by atomic number (working outward on ties), then reading the sense of rotation (clockwise = R, counterclockwise = S) with the lowest-priority group pointing away from the viewer. It requires no external reference compound and can, in principle, be applied unambiguously to any stereocentre in any molecule -- it is therefore called an absolute system. The D/LD/L system instead assigns a configuration by comparing a Fischer projection of the compound in question to that of a fixed, historically chosen reference compound, glyceraldehyde: a compound whose configuration at the relevant carbon matches D-glyceraldehyde's spatial arrangement is labelled D, and one matching L-glyceraldehyde is labelled L. Because this labelling depends entirely on that external comparison rather th …

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