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outline_sg_iv - Outline Study Guide for Unit IV Amines...

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Quinine: A Popular Amine with a Rich History The Cinchona tree, found in rain forests on the eastern slopes of the Andes, has long been revered for its medicinal properties. Most famously, its bitter bark is effective in preventing malaria. Upon receiving a shipment of Cinchona bark from South America in 1640, the British military went about developing a Cinchona tonic to protect its troops from the deadly disease while on missions in the tropics. H N H H The problem? The active component, quinine, is barely soluble in water (~0.5 g/L), meaning that a person would have to consume close to two liters of "tonic water" HO per day to get the recommended dose of quinine. The solution? Quinine is extremely soluble in ethanol (~1.2 kg/L). The British soldiers could soak the Cinchona bark in gin and drink just a few ounces of the concoction three times a day. Lime juice was used to H 3 CO disguise the bitter flavor of the quinine, and a cultural phenomenom was born! The modern version of the gin and tonic uses carbonated tonic water, first
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