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3. a. The reaction sequence shown in Scheme 5 demonstrates the synthesis of a substituted benzene derivative Q. NH2 NaNO2, HCI HNO3, H2SO4 CeHCINZ CHINO2

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3. a. The reaction sequence shown in Scheme 5 demonstrates the synthesis of a substituted benzene derivative Q. NH2 NaNO2, HCI HNO3, H2SO4 CeHCINZ CHINO2 0C N P Q Scheme 5 (i) Draw the structure of intermediate 0. (ii) Draw the mechanism for the transformation of aniline N to intermediate 0. (iii) Identify the reagent X used to convert compound 0 to the iodinated compound P. (iv) Identify the possible structures of compound Q. (v) Draw the mechanism for the transformation of intermediate P to compound Q. (vi) Account for the regiochemical outcome observed in the reaction forming compound

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