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(a) Give two syntheses for and explain which synthesis is

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

Problem 47SP Chapter 6

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 47SP

(a) Give two syntheses for  and explain which synthesis is better.

(b) A student wanted to synthesize methyl tert-butyl ether,  He attempted the synthesis by adding sodium methoxide to tert-butyl chloride, but he obtained none of the desired product. Show what product is formed in this reaction, and give a better synthesis for methyl tert-butyl ether.

Step-by-Step Solution:

Solution 47SP :

Step 1:

(a)

Here, we need to give two syntheses for  and explain which synthesis is better

Synthesis(1) shown below gives a better yield of the ether product. The 1st synthesis shown uses SN2 attack of a nucleophile on a 1o carbon. The 2nd synthesis requires attack on a more hindered 2o carbon. Synthesis(2) would give a lower yield of substitution with more elimination. The new bond formed is shown with different color.

Step 2 of 2

Chapter 6, Problem 47SP is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L. G. Wade Jr
ISBN: 9780321768414

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