Question

What product do you predict from the reaction of \(\mathrm{SCl}_{2}\) with benzene in the presence of \(\mathrm{AlCl}_{3}\) ? What product results if diphenyl ether is treated with \(\mathrm{SCl}_{2}\) and \(\mathrm{AlCl}_{3}\) ?

Short answer

Answer: When SCl2 reacts with benzene in the presence of AlCl3, chlorosulfonylbenzene is formed. When SCl2 reacts with diphenyl ether in the presence of AlCl3, chlorosulfonyldiphenyl ether is formed.

Step-by-step solution

Reaction of SCl2 with Benzene

When benzene is treated with SCl2 in the presence of AlCl3, an electrophilic aromatic substitution reaction can occur. SCl2 can act as an electrophile in the presence of AlCl3. The presence of AlCl3 helps in generating the electrophile by accepting a lone pair of electrons from the chlorine atom, forming an S=Cl+ complex which then reacts with benzene: 1. Benzene + SCl2 + AlCl3 → Chlorosulfonylbenzene + AlCl4- (Electrophilic aromatic substitution) The product formed is chlorosulfonylbenzene, where the chlorine and sulfur are attached to the same carbon in benzene.

Reaction of SCl2 with Diphenyl Ether

The reaction between diphenyl ether and SCl2 in the presence of AlCl3 involves electrophilic aromatic substitution also. Similar to the previous reaction, the electrophile is generated in the presence of AlCl3, and this electrophile will attack the electron-rich, activated aromatic ring of diphenyl ether: 1. Diphenyl ether + SCl2 + AlCl3 → Chlorosulfonyldiphenyl ether + AlCl4- (Electrophilic aromatic substitution) The product formed is chlorosulfonyldiphenyl ether, where the chlorine and sulfur are attached to the same carbon in one of the phenyl rings connected by the ether group.