Dolbier HW Solutions 556

Dolbier HW Solutions 556 - 650 AMINES nitrogen is more...

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nitrogen is more shielded than one bonded to oxygen, because nitrogen is less electronegative than oxygen. In one isomer the lowest f eld signal is a quaternary carbon; in the other it is a CH 2 group. The spec- trum shown in Figure 22.10 shows the lowest f eld signal as a CH 2 group. The compound is there- fore 2-amino-2-methyl-1-propanol, (CH 3 ) 2 CCH 2 OH. = NH 2 This compound cannot be prepared by reaction of ammonia with an epoxide, because in basic so- lution nucleophiles attack epoxides at the less hindered carbon, and therefore epoxide ring opening will give 1-amino-2-methyl-2-propanol rather than 2-amino-2-methyl-1-propanol. SELF-TEST PART A A-1. Give an acceptable name for each of the following. Identify each compound as a primary, secondary, or tertiary amine.
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