a) Provide structures for the reagent(s) or product(s) of the following reaction sequence. If a mixture of ortho and para products is expected, it is sufficient to draw one and name the other. "No Reaction" may be a correct answer in some cases. 0H soon2 '? w __ ? a 0 3b 3a 3c 0

b) A student in our organic lab, who may not have been well-prepared for this experim-t, conducted the reaction below and obtained a single product (3a) in very good yield. However the spectral data that was collected suggested that this product was not the compound that was anticipated. The available data included the 1H and I'1'C NMR spectra shown below, as well as a mass spectrum with a molecular ion at mfi' of 100 (C6H120). Propose a structure for this product that would be consistent with the data that was obtained 1) Mg, ether 2) H200 M 3L" I" \N Br 3:! 39 2H 1H .- - 2H 6H . ill _ ' _ I ll . l . . . 4 |. ' u. _.