Which of the following best explains why the synthetic route shown below would be unsuccessful?

Question

Quizplus · Accepted Answer

The synthetic route shown involves the formation of an alkynide anion by the reaction of sodium amide with the terminal alkyne. This alkynide anion is then used to perform two consecutive substitution reactions with 1-bromopropane (step 1) and t-butyl bromide (step 2). However, the alkynide anion formed is likely to facilitate an E2 elimination reaction with t-butyl bromide rather than the desired substitution reaction. This is because t-butyl bromide is a hindered substrate that favors elimination reactions. Therefore, the synthetic route is unlikely to work due to the unwanted E2 reaction.

Which of the Following Best Explains Why the Synthetic Route