Learn more about the benzene reactions at vedantu.com. It does not readily react with organic substances. Halogenation is an example of electrophillic aromatic substitution. However, halogens are not electrophillic enough to break the aromaticity of benzenes, which require a catalyst to activate. With aluminum bromide as a Lewis acid, we can mix Br2 with AlBr3 to give us Br+. The elements present in organic compounds are carbon and hydrogen. The presence of Br+ is a much better electrophile than Br2 alone. In electrophilic aromatic substitutions, a benzene is attacked by an electrophile which results in substition of hydrogens. . Considering the exothermic rates of aromatic halogenation decreasing down the periodic table in the Halogen family, Flourination is the most exothermic and Iodination would be the least. Bromination is acheived with the help of AlBr3 (Lewis acid catalysts) as it polarizes the Br-Br bond. The catalyst is either aluminum chloride (or aluminum bromide if you are reacting benzene with bromine) or iron. Benzene reacts with bromine or chlorine in an electrophilic substitution reaction only in the presence of a catalyst which is either chloride or iron. Step 2: The π electrons of aromatic C=C behave as a nucleophile which attacks the electrophilic Br and displaces iron tetrabromide. Facts and mechanism for the halogenation (chlorination and bromination) of benzene - an electrophilic substitution reaction between benzene and chlorine or bromine THE HALOGENATION OF BENZENE This page gives you the facts and a simple, uncluttered mechanism for the electrophilic substitution reaction between benzene and chlorine or bromine in the presence of a catalyst such as … For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. Watch the recordings here on Youtube! Benzene reacts with chlorine or bromine in an electrophilic substitution reaction, but only in the presence of a catalyst. Benzene reacts with bromine or chlorine in an electrophilic substitution reaction only in the presence of a catalyst which is either chloride or iron. With aluminum bromide as a Lewis acid, we can mix Br2 with AlBr3 to give us Br+. To menu of electrophilic substitution reactions. The halogenation of benzene Substitution reactions Benzene reacts with chlorine or bromine in the presence of a catalyst, replacing one of the hydrogen atoms on the ring by a chlorine or bromine atom. 2Fe +3Cl2→ 2FeCl3 2Fe + 3Br2→2FeBr3 Step 3: The proton is removed from sp3 C and bears the Bromo group that reforms C=C and aromatic system generates HBr and regulates active catalyst. $C_6H_6 + Br_2 \rightarrow C_6H_5Br + HBr$. However, in the case of elemental fluorine (F2) we will need some proper apparatus and fulfil certain conditions. Hence it being an electrophilic aromatic SUBSTITUTION. (where X= Br or Cl, we will discuss further in detail later why other members of the halogen family Flourine and Iodine are not used in halogenation of benzenes). 1. Example, the addition of bromine to ethane. Step 1: The bromine reacts with Lewis acid to create a complex that makes bromine more electrophilic. This allows the other bromine atom to leave with the AlBr3 as a good leaving group, AlBr4-. 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