Posted: December 1st, 2016
A student wanted to synthesize 4-(5-methylhex-3-yn-1-yl)phenol. The student\’s key step was to be the SN2 reaction of an acetylide with 4-(2-bromoethyl)phenol. However, the student isolated none of the desired product. What went wrong? Draw the two products the student isolated instead. Assume a 1:1 mixture of reagents
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