(e)According to the principle applied in part (a) (alkyl groups increase basicity, aryl groupsdecrease it), the order of decreasing basicity is as shown:22.27Nitrogensais the most basic and the most nucleophilic of the three nitrogen atoms of physostigmineand is the one that reacts with methyl iodide.The nitrogen that reacts is the one that is a tertiary alkylamine. Of the other two nitrogens,sbisattached to an aromatic ring and is much less basic and less nucleophilic. The third nitrogen,sc, isan amide nitrogen; amides are less nucleophilic than amines.22.28(a)Looking at the problem retrosynthetically, it can be seen that a variety of procedures are avail-
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.