Question

Draw the structure of the product of each step in the following three-step synthesis. Show the formal charges, if applicable. As a start, the benzene ring is drawn for you in each product. Although the first step produces a mixture of isomers, the para isomer is isolated as the sole product of interest and used in the second step. Give only the major product for the second and third steps.

Answer 1

Step 1: Toulene is treated with Br3 and FeBr3 to form 1-bromo-4-methylbenzene.

                           

            

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Step 2: 1-bromo-4-methylbenzene is HNO3 and H2SO4 to form 5-bromo-2-methyl phenyl nitrate.

                          

                 

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Step 3: 5-bromo-2-methyl phenyl nitrate is treated with Br3 and FeBr3 to form 3,5-dibromo-2-methylphenyl nitrate.

        

Answer 2

(para-bromo toluene) +HNO3/H2SO4= (4-bromo-2-nitrotoluene)+Br2/FeBr3= 2,4-dibromo-6-nitrotoluene DONT FORGET THE FORMAL CHARGES:))