(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.
Solution 47SP :
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.