Solution Found!
(a) Give two syntheses for and explain which synthesis is
Chapter 8, Problem 47SP(choose chapter or problem)
(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)
Questions & Answers
QUESTION:
(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)
ANSWER:
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.
