Questions/Stereochemistry/Why are quaternary a...
Chirality & SymmetryStereochemistry

Why are quaternary ammonium salts (e.g., [N(R1)(R2)(R3)(R4)]+[N(R_1)(R_2)(R_3)(R_4)]^+ ) optically active?

Expert Answer

Unlike amines, quaternary salts cannot undergo pyramidal inversion (no lone pair), so the chiral configuration is locked and resolvable.

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