Directing Nitration

Chemistry Level 3

Benzene is added to a solution of $\ce{Br2}$ and $\ce{Fe}$ . The major product is then added to a solution with an excess ( $\ce{Xs}$ ) of $\ce{HNO3}$ and $\ce{H2SO4}$ .

Determine the total number of major products formed after excess nitration.

Note: Be aware that some groups on a benzene are $\text{ortho/para}$ directing while others direct $\text{meta}$ .

David's Organic Chemistry Set

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1 solution

David Hontz
Jun 29, 2016

Once $\text{bromo benzene}$ is formed, the bromine will begin adding $\text{nitro}$ groups ortho and para to it. From then on, bromine will continue to add $\text{nitro}$ groups ortho and para to itself while the $\text{nitros}$ will assist in adding to spots that are, at the same time, meta to themselves. There is only $\boxed{1}$ major product formed: $\text{2,4,6-trinitro phenylbromide}$ .

Isn't it like when 2 nitro and 1 Bromine group is already attached the ring is too much deactivated(owing to -R and -I effect of Nitro and -I effect of Bromine).Further Nitration won't be possible I guess.

Spandan Senapati - 3 years, 11 months ago

Directing Nitration

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