Question #67d83

1 Answer
Ernest Z.
Dec 30, 2017

There are three chiral centres in atropine sulfate.

Explanation:

I have marked them with asterisks in the diagram below.

Atropine sulfate
(Adapted from Sigma-Aldrich)

Carbon #3# of the azabicyclo[3.2.1]octane system appears to be chiral. However, it sits on an internal plane of symmetry passing through atoms #3, 8#, and the mid-point of the #"6-7"# bond, so it is achiral.

Atoms #1# and #5# are on opposite sides of this plane, so they are part of a meso system.

It is carbon #2# of the propionic acid chain that contributes to the optical activity of the compound.

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