BONUS QUESTION (10 points)
Consider the following transformation shown below. Write a reasonable mechanism to account for the
formation of the anthracene product. Hint: This mechanism likely involves both a benzyne reactive
intermediate (via E2 elimination of the bromobenzene) and a retro [2,3]-cycloaddition step with the
tetrahydrofuran, among others. Note that the R group in the alkyllithium reagent (a strong base) is not
part of the product.
Br
RLi