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A student wanted to use the Williamson ether synthesis to

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 35SP Chapter 11

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 35SP

A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2 goes best on primary halides and tosylates, so he madeethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.

(a) What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the sN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.

(b) What would have been the best synthesis of (R)-2-ethoxybutane?

(c) How can this student convert the rest of his bottle of (S)-butan-2-ol to (R)-2-ethoxybutane?

Step-by-Step Solution:
Step 1 of 3

Solution 35SP

a) (R) enantiomer of 2 - ethoxybutane is obtained

b)...

Step 2 of 3

Chapter 11, Problem 35SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

The full step-by-step solution to problem: 35SP from chapter: 11 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. Since the solution to 35SP from 11 chapter was answered, more than 543 students have viewed the full step-by-step answer. The answer to “A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2 goes best on primary halides and tosylates, so he madeethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.(a) What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the sN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.(b) What would have been the best synthesis of (R)-2-ethoxybutane?(c) How can this student convert the rest of his bottle of (S)-butan-2-ol to (R)-2-ethoxybutane?” is broken down into a number of easy to follow steps, and 116 words. This full solution covers the following key subjects: ethoxybutane, synthesis, sodium, bottle, butan. This expansive textbook survival guide covers 25 chapters, and 1336 solutions.

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