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Solutions_Manual_for_Organic_Chemistry_6th_Ed 444

Solutions_Manual_for_Organic_Chemistry_6th_Ed 444 - 19-1...

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CHAPTER 19-AMlNES 19-1 These compounds satisfy the criteria for aromaticity (planar, cyclic 1t system, and the Huckel number of 4n + 2 1t electrons): pyrrole, imidazole, indole, pyridine, 2-methylpyridine, pyrimidine, and purine. The systems with 6 1t electrons are: pyrrole, imidazole, pyridine, 2-methylpyridine, and pyrimidine. Th� systems with 1 0 1t electrons are: indole and purine. The other nitrogen heterocycles shown are not aromatic because they do not have cyclic 1t systems. 19-2 (a) CH3 I H3C- -NH2 CH3 (d) 19-3 (a) pentan-2-amine (c) 3-aminophenol (or meta-) (b) (e) NH2 I CH3-CHCHO (b) N-methylbutan-2-amine (d) 3-methylpyrrole (c) Q N H C / .. .. CH 3 3 (f) (e) trans-cyclopentane-l,2-diamine (f) cis-3-aminocyclohexanecarbaldehyde 19-4 (a) resolvable: there are two asymmetric carbons; carbon does not invert (b) not resolvable: the nitrogen is free to invert (c) not resolvable: it is symmetric (d) not resolvable: even though the nitrogen is quaternary, one of the groups is a proton which
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