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There are two different ways of making 2-ethoxyoctane from octan-2-ol using the
Chapter 14, Problem 14-47(choose chapter or problem)
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 \(-8.24^{\circ}\) is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoctane with a specific rotation of \(-15.6^{\circ}\). 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.
Questions & Answers
QUESTION:
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 \(-8.24^{\circ}\) is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoctane with a specific rotation of \(-15.6^{\circ}\). 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.
ANSWER:Step 1 of 2
The functional group of Octan-2-ol is the alcohol group. It can be prepared in two methods.
Octan -2-ol is treated with Sodium metal to form a sodium alkoxide ion. This ion is treated with ethyl iodide to form 2-ethoxyoctane.
The configuration of the product is the same as the configuration of the starting reactant.
The reaction is as follows.
The final product of the reaction is as follows.
