What are the chiral centers of the molecule of nicotine?

1 Answer
Nov 24, 2015

There's only one, and it's S.

The highest to lowest priority is (1,2,3,4):

  • tertiary amine (highest atomic number here; #-"NC"_2#)
  • aromatic #sp^2# (taken similar to tert-butyl, i.e. #-"CC"_3#)
  • methylene (#-"CH"_2#)
  • hydride (#-"H"#)

You get that from going clockwise and crossing the hydride, but since the hydride is facing forwards rather than backwards, the configuration is the reverse of R, which is S.