QUESTION 1

Two alkaloids isolated from plant

sources which have pharmaceutical
use are shown to the right. Atropine
is used as an antispasmodic agent for
treatment of colitis and cocaine is
used as both an anaesthetic and
central nervous system stimulant.

(a) Can these compounds be distinguished, based on the mass of the YES / NO
molecular ions in the mass spectra? (Circle one.)
Justify your choice.

(b) Which compound would be expected to have an atropine / cocaine

absorption in the UV at longest wavelength? (Circle one.)
Justify your choice.

(c) Can these compounds readily be distinguished by IR spectroscopy?

YES / NO
Justify your choice. (Circle one.)

(d) For the sp3 hybridised carbons in atropine seven signals are
observed in the proton decoupled 13C NMR spectrum.

(i) Label these carbon environments on the structure

of atropine to the right.

(ii) These signals are found in the range O

to 
O
(e) In the 1H NMR spectrum for atropine the signal for the circled hydrogen would be

(i) expected in the range to 

(ii) split into lines.

Justify your answer.