A student was given the task of synthesizing an organic compound (Compound E, below) using a series of basic organic chemistry reactions. The reaction sequence is as follows. First, compound A was halogenated to produce compound B using Br2, resulting in the anti addition of Br and Br across the double bond. The next step required the substitution of the hydroxyl substituent, so the compound was treated with tosyl-chloride to activate the oxygen (compound C), and then treated with sodium azide to complete the substitution and form compound D.
The student successfully created compound E but unfortunately forgot to label his reagents for the reaction for D to E. The reaction involved the electrophilic addition of acetaldehyde to the aromatic ring of compound D.
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