If two identical substituents are attached to an sp3-hybridized atom, the descriptors pro-R and pro-S are used to distinguish between the two. Replacing the pro-R substituent results in an R chirality center at the original sp3-hybridized atom, and vice versa.
A trigonal planar sp2-hybridized atom can be converted to a chirality center when a substituent is added to the re or si face of the molecule.
- John McMurry. Organic Chemistry, 6ed, Brooks/Cole, 301-303.
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