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

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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There are two different ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. When pure
(-)@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@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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