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(a) State the classification (aromatic, non-aromatic, or anti-aromatic) for each of the compounds A and B shown below. Draw each of the compounds and provide your classification adjacent to the structure. HN H3CO OCH3 A B [1] (b) For compounds C and D shown below, indicate the two most susceptible positions to electrophilic substitution on each aromatic ring. Do this by copying each of the compounds into your response; then, indicate both sites on each compound with an arrow (Note: the response requires two arrows per compound). NH2 CH3 -CH3 NOZ с D [2] (c) Product E is created by treatment of compound with nitric acid, sulfuric acid and heat. Draw the structure of E formed in this reaction. NH2 CH, HNO3 H2SO4 heat E с [1] 1

(d) Draw the product G that is formed by treating F with aqueous sodium methoxide. ON. NaOCHz (aq) G SOGH F [1] (e) Benzene (H) is converted to compounds 1-M with a series of reactions detailed below. Provide the reagent(s)(x) required to convert benzene (H) to compound I and the reagent(s)(Y) required to convert benzene (H) to compound K. Draw the most favoured product for each of the transformations to the final compounds J, L and M. (Note: For your responses to this question, ensure that you label each of your figures/reagents with X or Y.. etc.). 1. HNO3, H2SO4, heat 2. H2 & Pd/C reagents X J V ( L 1. Zn( Hg) & HCI 2. HNO3, H2SO4 heat reagents Y HNO3, H2SO4, heat K (5)