Question

(V) 10pts. When aniline (C6H3-NH2) reacts with bromonium ion (NO2. the nitro group can become bonded to a carbon at one of the three possible positions: ortho, meta, and para to the -NH2 group in the benzene ring. Consider meta and ortho attack and draw RESONANCE STRUCTURES for the carbocations that result when NO2 undergoes electrophilic aromatic substitution to aniline. Then, on the basis of these resonance structures, explain whether the --NH2, group.is meta director, or ortho/para director. Show which resonance structures have extra stability or instability to support your claim above. CTURES for the carbconsider meta and orthortha, meta, and

Answer 1

The reaction between aromatic compound and an electrophile proceeds via aromatic electrophilic substitution reaction .

In the aromatic electrophilc substitution reaction between aniline and NO2+ the ortho and meta substituted products will be favourable as compare to meta substituted product due the electron donating effect of —NH2 group towards benzene ring .

The detail explanation is shown below on the basis of resonance stabilization factor .

02 Formation of metu sulestituted product in Formati meta su NY NO, -44 (m) Formation of ortho substituted product in M2 OM The number of carbocations that reesult when som undergoes electrophilic aromatic substitution to amiline will be higher for artha/ para substitution as compare to meta substitution Thens ortho / para substituted prodricts will be -NH2 is ortho/para d&rector for aromatic electewphilic substitution by This is due to gaim of extra resonance stabilization inrobring ebertron donating mesomeria Tomo esbect with benzene ving a