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What is the stepwise chemical reaction mechanism involved in the preparation of 2,4,6-trinitrotoluene from toluene and nitric acid, and what are the conditions required for each step?

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The preparation of 2,4,6-trinitrotoluene  TNT  from toluene and nitric acid involves a series of nitration reactions. The overall process can be divided into three main steps, each involving the addition of a nitro group  -NO2  to the toluene molecule. The reaction mechanism for each step is electrophilic aromatic substitution.1. First Nitration  Mono-nitration :Toluene  C6H5CH3  reacts with a mixture of concentrated nitric acid  HNO3  and concentrated sulfuric acid  H2SO4  to form 2-nitrotoluene and 4-nitrotoluene as major products. The concentrated sulfuric acid acts as a catalyst and helps in the formation of the nitronium ion  NO2+ , which is the electrophile in this reaction.Reaction conditions: Temperature around 0-30C, and a mixture of concentrated HNO3 and H2SO4  1:1 ratio .Mechanism:a  Formation of nitronium ion  NO2+ : HNO3 + 2H2SO4  NO2+ + H3O+ + 2HSO4-b  Electrophilic attack: The nitronium ion  NO2+  attacks the aromatic ring of toluene, forming a resonance-stabilized carbocation.c  Deprotonation: A proton from the carbocation is removed by the HSO4- ion, regenerating the aromatic ring and forming the nitrotoluene product.2. Second Nitration  Di-nitration :The mono-nitrotoluene product  either 2-nitrotoluene or 4-nitrotoluene  is further nitrated using a mixture of concentrated nitric acid and concentrated sulfuric acid to form dinitrotoluene isomers.Reaction conditions: Temperature around 30-50C, and a mixture of concentrated HNO3 and H2SO4  1:1 ratio .The mechanism for this step is similar to the first nitration, with the nitronium ion attacking the mono-nitrotoluene molecule and forming a resonance-stabilized carbocation, followed by deprotonation to form the dinitrotoluene product.3. Third Nitration  Tri-nitration :The dinitrotoluene isomer  2,4-dinitrotoluene  is further nitrated using a mixture of concentrated nitric acid and concentrated sulfuric acid to form 2,4,6-trinitrotoluene  TNT .Reaction conditions: Temperature around 60-80C, and a mixture of concentrated HNO3 and H2SO4  1:1 ratio .The mechanism for this step is also similar to the previous nitration steps, with the nitronium ion attacking the dinitrotoluene molecule and forming a resonance-stabilized carbocation, followed by deprotonation to form the TNT product.In summary, the preparation of 2,4,6-trinitrotoluene  TNT  from toluene and nitric acid involves three nitration steps, each with electrophilic aromatic substitution as the reaction mechanism. The conditions for each step involve increasing temperatures and a mixture of concentrated nitric acid and sulfuric acid.

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