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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