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Answer ALL parts a) - c). For the reduction of nitro derivatives such as nitrobenzene 1 to aniline 2 , reaction condition using a combination

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Answer ALL parts a) - c). For the reduction of nitro derivatives such as nitrobenzene 1 to aniline 2 , reaction condition using a combination of a palladium catalyst, molybdenum hexacarbonyl and water have been developed. When the reduction is performed in the presence of para-tolylboronic acid, the amide 4 is obtained. a) Draw a catalytic cycle for the amide formation. Which additional reagent is necessary for the amide formation to proceed? b) Using the reaction conditions shown above, draw the necessary starting materials to make amide 5. c) When the aromatic nitro compound is replaced with 1-nitropentane 6 and the boronic acid is replaced with the arylbromide 7 , a bicyclic product 8 is obtained. Draw the structure of this product 8 containing a core structure of biologically active pharmaceuticals. 6 7

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