There are two different ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. When pure

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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 -15.6°. When pure (-)-octan-2ol 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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Organic Chemistry

ISBN: 978-0321768414

8th edition

Authors: L. G. Wade Jr.

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