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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 ISBN: 9780321768414 33

Solution for 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 \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{3}\), and explain which synthesis is better.


(b) A student wanted to synthesize methyl tert-butyl ether, \(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\). He attempted the synthesis by adding sodium methoxide \(\left(\mathrm{CH}_{3} \mathrm{ONa}\right)\) 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.

Equation Transcription:

Text Transcription:

(CH_3)_2CH-O-CH_2CH_3

CH_3-O-C(CH_3)_3

(CH_3ONa)

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