Which of these 4 molecules are chiral molecules and chiral centers?

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1 Answer
Aug 3, 2017

Looks like #D# is chiral to me, and it would have a chiral center on the tertiary carbon external to the bottom-left ring.


Let the molecules be labeled #A,B,C,D# from left to right (first row = #A,B#, second row = #C,D#).

Well, the tertiary carbon would be a first candidate, if not for the plane of symmetry around it in #B#:

This is due to the identical carbonyls and #"N"-"H"# groups on the left and right side of the benzene ring. So, we can disregard that carbon, because with a plane of symmetry, it can never be chiral. Given the plane of symmetry in the entire molecule, #B# is achiral.

Since we can disregard the tertiary carbon, it follows that #A# and #C# are also not chiral (the only difference with respect to #B# is #"H" harr "CH"_3#).

Further examination of #A# shows two identical carbonyls on either side of the #"N"-"CH"_3#, so the nitrogen there is also not a chiral center (not to mention, it only has three electron groups).

So, that only leaves #D# being chiral, due to the tertiary carbon external to the ring, surrounded by:

  • #"CH"_3#
  • #"CH"_2-"CH"_3#
  • #"H"#
  • The carbon we called tertiary earlier, on the bottom-left ring.

Due to having four different groups around it, #bbD# has one chiral center and is a chiral molecule overall.