Dolbier HW Solutions 526 - 620 AMINES(e According to the...

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( e ) According to the principle applied in part ( a ) (alkyl groups increase basicity, aryl groups decrease it), the order of decreasing basicity is as shown: 22.27 Nitrogen a is the most basic and the most nucleophilic of the three nitrogen atoms of physostigmine and 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, b is attached to an aromatic ring and is much less basic and less nucleophilic. The third nitrogen, c , is an 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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