3. Note: If benzene ring is taken as substituent then. Electrophilic substitution reaction of haloarenes. React it with CuCl (Sandmeyer’s Rxn) or Cu Powder (Gatterman Rxn) to form Chlorobenzene. If you are on a personal connection, like at home, you can run an anti-virus scan on your device to make sure it is not infected with malware. Not worth the effort, just buy some benzene. A wide range of groups that can be used to replace N2 including halide, SH−, CO2H−, OH−. Ltd., Kolkatta, 2007. As a result, C – X bond in haloarenes is shorter and hence stronger as compared to the C – X bond of haloalkanes. Action with cuprous cyanide : Chlorobenzene when heated with cuprous cyanide (CuCN) at 2000Cin the presence of pyridine gives phenyl cyanide. This reaction is known as Wurtz-Fitting reaction. Nitrobenzene : Laboratory preparation, Properties and Uses. Reaction with aq. Haloarenes can be converted into the corresponding arenes by reduction with Ni-Al alloy in presence of alkali. Chlorobenzene is prepared by treating benzene diazonium chloride with copper powder dissolved in HCl. Thus, cleavage of C – X bond becomes difficult which makes it difficult towards nucleophilic substitution reaction. The diazo group (N2) can be replaced by many other groups, usually anions, giving a variety of substituted phenyl derivatives: These transformations are associated with many named reactions including the Schiemann reaction, Sandmeyer reaction, and Gomberg-Bachmann reaction. This reaction is called Sandmeyer reaction. Q) Why is it difficult to undergo nucleophilic substitution reaction in haloarenes? It exists as a colourless solid that is soluble in polar solvents including water. Boiling and melting point : Haloarenes have higher boiling point than arenes of comparable molecular masses. Halogenation : Halogenation takes place in the presence of iron or FeCl3 or anhydrous AlCl3 as a catalyst. 1. Convert phenol into chlorobenzene by reacting phenol with PCl3/Pcl5(Sn2 mechanism) or SOCl2 (SNi mechanism) Another way to prevent getting this page in the future is to use Privacy Pass. Chlorobenzene can be obtained by the direct chlorination of benzene in cold, dark and in the presence of halogen carrier Lewis acids such as AlCl3, FeCl3,etc. NH3 : Chlorobenzene when heated with aq. This reaction is the modification of Sandmeyer’s reaction and called Gattermann reaction. Reaction with aq. When aniline is treated with sodium nitrite (NaNO2) and dil.HCl at temperature below 50C, benzene diazonium chloride is obtained. Method of preparation: The reaction of aniline (aromatic amine) with nitrous acid results in the formation of the diazonium salt. Haloarenes are colourless liquid or crystalline solid. Chlorobenzene is prepared by treating benzene diazonium chloride with copper powder dissolved in HCl. Eg. ammonia in the presence of cuprous oxide (Cu2O) at 2000C under a pressure of 60 atm gives aniline. The resonating structures of haloarene are as follows: From the resonating structures it is clear that ortho and para positions are relatively rich in electron density and hence incoming electrophile attacks at these positions to give ortho and para substituted products.


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