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4. (a) Please provide two different means of preparing aniline below using a reduction reaction and a rearrangement reaction NH2 -NH NaBry NaOH, Bra H2O

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4. (a) Please provide two different means of preparing aniline below using a reduction reaction and a rearrangement reaction NH2 -NH NaBry NaOH, Bra H2O Hoffman + BB: 002 Reduction Reaction NH Rearrangement Reaction (b) Please provide two different means for synthesizing the tertiary amine below from a ketone and an amide using single-step reactions. NOBH HC "CH3 ketone amide 5. Provide reasonable step-by-step mechanisms for the following transformations. Use curved arrows to show all electron movement, and be sure to show all intermediates. OH/Br2 H20 NH2 + CO2 NH2 heat, H2O NH2 + N2 + CO2 6. Provide concise multi-step syntheses for the following transformations. Be sure to show all reagents and intermediate products. NH2 H. multiple steps Ph Ph Ph

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