C2. Questions l. Shown are 2 resonance structures of the diazonium ion a. Add the correct formal charges to each structure. 1pt b. Indicate the hybidiztion at each nitrogen as sp, sp2 or sp3, 2pts. N4 N3 N2 N N 2. Congo Red is a commercial azo dye used extensively in biochemistry, histology and microbiological epidemiology. Propose a synthesis of this dye using a diazonium salt and an activated aromatic compound, your reactants should form only one isomer. 2pts SO3H HOS N N N N NH H3N Congo Red 3. The structures of many dyes change in acidic and basic solution. Draw the structure the dye below would have in a solution of 3M HCl (pHkl) water (pH 7) and 3M NaOH (pH 14). The pKas of the functional groups are given, everything is in its acid form. 3pts OH pKa 10 pH
