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

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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions

Section30.8: Some Examples Of Sigmatropic Rearrangements

Problem 9P: When a 2, 6-disubstituted allyl phenyl ether is heated in an attempted Claisen rearrangement,...

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