There are two different ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. When pure 1-2-octan-2-ol of specific rotation -8.24° is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoctane with a specific rotation of -15.6o.When pure(-)-octan-2-ol is treated with tosyl chloride and pyridine and then with sodium ethoxide, the product is also 2-ethoxyoctane. Predict the rotation of the 2-ethoxyoctane made using the tosylation/ sodium ethoxide procedure, and propose a detailed mechanism to support your prediction.
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