which one of the reactions below would produce the following compound in high yield?
which one of the reactions below would produce the following compound in high yield?
Answer
Explanation:
Step1: Recall Williamson ether synthesis
The compound is an ether and can be synthesized via Williamson ether synthesis. In Williamson ether synthesis, an alkoxide ion reacts with an alkyl - halide. The alkoxide should attack the less - hindered carbon attached to the halogen for a high - yield reaction.
Step2: Analyze the options
The alkoxide should be the nucleophile and the alkyl - halide should be the electrophile. The reaction with the least steric hindrance around the carbon - halogen bond will give the highest yield. The first option with the alkoxide $\ce{R - O^-}$ attacking the primary alkyl - halide (the carbon attached to $\ce{Br}$ is primary) is the most favorable for a high - yield reaction as the $S_N2$ mechanism (which is the mechanism of Williamson ether synthesis) proceeds best with primary alkyl halides.
Answer:
The first reaction (where the alkoxide $\ce{R - O^-}$ attacks the primary alkyl - halide) would produce the compound in high yield.