Organic chemistry

Exercise 4

    

a) Nitrobenzene is converted by the action of chlorine in the presence of $ AlCl_3$ to chloronitrobenzene . What is the main isomer obtained in this reaction? Justify!

We get the m -chloronitrobenzčne: Indeed, due to the mesomerism, ortho and para positions of nitrobenzene are depleted in electrons and therefore hardly suited to the attack of the electrophilic agent $Cl^+$

b)In aniline, the amine group participates in the mesomerism the benzene ring. Write contributive forms to this mesomerism and discuss the influence of the mesomerism on the basicity of aniline!

Due to the mesomerism, the electron pair of the $N$ atom of aniline is less available than aliphatic amines to capture $H^+$ ions: Aniline is less basic than the latter.