Chapter 19: Q15P (page 999)
Propose a mechanism to show the individual alkylations that form this quaternary ammonium salt.
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Propose a mechanism for the sulfonation of pyridine, and point out why sulfonation occurs at 3-position.
When the (R,R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the major product is the Hofman product.
Within each structure, rank the indicated nitrogens by increasing basicity.
Rank the amines in each set in order of increasing basicity.
Reductive amination of aldehydes and ketones is a versatile method for attaching alkyl groups to amines, but the alkyl group is restricted to a 1 0or 20carbon by this method. Prof. Phil Baran of Scripps Research Institute has reported (Science, 2015, 348(6237), 886-891) a novel way to reduce an aromatic nitro group and add the resulting amine to an alkene so that the aromatic amine is bonded to a carbon- all in a continuous sequence of reactions. For example:
Predict the products using these starting materials, all of which are reported in this paper.
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