Chapter 15, Problem 49P

16-54 Several poisonous plants, including Atropa

belladonna, contain the alkaloid atropine. The name “belladonna” (which means “beautiful lady”) probably comes from the fact that Roman women used extracts from this plant to make themselves more attractive. Atropine is widely used by ophthal mologists and optometrists to dilate the pupils for eye examination.

1. Classify the amino group in atropine as primary, secondary, or tertiary.

Locate all stereocenters in atropine.

Account for the fact that atropine is almost insoluble in water (1 g in 455 mL of cold water) but atropine hydrogen sulfate is very soluble (1 g in 5 mL of cold water).

Account for the fact that a dilute aqueous solution of atropine is basic (pH approximately 10.0).