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In the first step, the reaction is only run to 10% to 15% conversion to prevent the second addition of a chlorine atom to the desired chlorobenzene. Despite this, the overall selectivity of the reaction is 70% to 85%. This second addition can be reversed using the Hooker modification, though it is also costly.
Photochlorination is a chlorination reaction that is initiated by light. Usually a C-H bond is converted to a C-Cl bond. Photochlorination is carried out on an industrial scale. The process is exothermic and proceeds as a chain reaction initiated by the homolytic cleavage of molecular chlorine into chlorine radicals by ultraviolet radiation ...
Iodobenzene reacts with chlorine to give the complex, iodobenzene dichloride, [4] which is used as a solid source of chlorine. Iodobenzene can also serve as a substrate for the Sonogashira coupling, Heck reaction, and other metal-catalyzed couplings. These reactions proceed via the oxidative addition of iodobenzene.
This reaction is related to several classic named reactions: The acylated reaction product can be converted into the alkylated product via a Clemmensen or a Wolff-Kishner reduction. [17] The Gattermann–Koch reaction can be used to synthesize benzaldehyde from benzene. [18] The Gatterman reaction describes arene reactions with hydrocyanic acid ...
The reaction mechanism for chlorination of benzene is the same as bromination of benzene. Iron(III) bromide and iron(III) chloride become inactivated if they react with water, including moisture in the air. Therefore, they are generated by adding iron filings to bromine or chlorine. Here is the mechanism of this reaction:
Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: [3] C 6 H 5 CH 3 + Cl 2 → C 6 H 5 CH 2 Cl + HCl. In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. [4]
The nitration of benzene is achieved via the action of the nitronium ion as the electrophile. The sulfonation with fuming sulfuric acid gives benzenesulfonic acid. Aromatic halogenation with bromine, chlorine, or iodine gives the corresponding aryl halides. This reaction is typically catalyzed by the corresponding iron or aluminum trihalide.
The Sandmeyer reaction provides a method through which one can perform unique transformations on benzene, such as halogenation, cyanation, trifluoromethylation, and hydroxylation. The reaction was discovered in 1884 by Swiss chemist Traugott Sandmeyer , when he attempted to synthesize phenylacetylene from benzenediazonium chloride and copper(I ...