Question: Convert benzene to 4-bromonitrobenzene.

My attempt:

enter image description here

Answer given:

enter image description here

Is my solution correct? Can aryl halodes react directly with $\ce{AgNO2}$ to form aryl nitrate?

  • 3
    $\begingroup$ AgNO2 may react with the two bromine atoms. $\endgroup$
    – Maurice
    Jul 3, 2021 at 19:29
  • 2
    $\begingroup$ Or, in this case, with neither - this is a method for aliphatic nitro compounds not aromatic. $\endgroup$
    – Mithoron
    Jul 3, 2021 at 20:03
  • 1
    $\begingroup$ (1) The bromine workup in your answer can be quite messy. If you increase the concentration of bromine, it can lead multiple isomer(both o- and p-isomer). It can also lead to formation of the tribromo- compound. (2) Why do you think AgNO2 will react with one bromine atom? (3) AgNO2 does react more with alkyl halides than aromatic halides $\endgroup$ Jul 4, 2021 at 5:10


Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.