Nutmeg-Model Kit Exercise-Markovnikov’s Rule

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In the spirit of the holiday season, nutmeg occurred to me as a blog-worthy source of material. This eggnog enhancement was originally grown exclusively in the Banda Islands west of New Guinea. Portugal annexed these islands in 1512 in order to control the nutmeg trade. They did so for nearly a century before ceding control of all but one of the islands to the Dutch. The outlier, the island of Run, was controlled by Great Britain. In 1667 the British traded Run to the Dutch in exchange for the island of New Amsterdam, aka Manhattan. The Dutch held a monopoly over the nutmeg trade until the early 19th century when, during the Napoleonic wars, the British invaded the Banda Islands, absconded with a bunch of nutmeg nuts, and planted them on the island of Grenada.

Nutmeg contains a potpourri of fragrant organic compounds, including, but not limited to d-pinene, limonene, d-borneol, l-terpineol, geraniol, safrol, and myristicin. Hydration of limonene generates terpineol. This transformation provides a good example of Markovnikov’s rule and is the basis for the Molecula exercise outlined below. Cheers!

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