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The concentrated sulfuric acid acts as a catalyst. Jmol.jmolCheckbox(jmolApplet0,"zoom 300","zoom 100","Zoom",false);Jmol.jmolBr() It is also possible to get a third nitro group attached to the ring (in the 5 position). This website uses cookies to improve your experience while you navigate through the website. And that puts a nitro group onto your benzene ring, in place of this proton. NO 2 +) formed by the loss of water from the nitric acid H 2 SO 4 + HNO 3 + C 6 H 6 | Nitration of Benzene. Jmol.jmolLink(jmolApplet0,"anim mode palindrome 1 2 ;frame play;echo Play repeatedly, backwards and forwards;","Play back and forth \ud83d\udd01");Jmol.jmolBr() They are used widely as precursors and chemical intermediates. When benzene is heated with concentrated sulfuric acid ( H 2 SO 4) and concentrated nitric (HNO 3) acid, nitrobenzene is given as the product. We'll assume you're ok with this, but you can opt-out if you wish. The mixture is held at this temperature for about half an hour. This reaction proceeds via the formation of an electrophilic nitronium ion (NO 2 + ) from nitric acid (HNO 3 ), … They are used widely as precursors and chemical intermediates. Out of these cookies, the cookies that are categorized as necessary are stored on your browser as they are as essential for the working of basic functionalities of the website. Halogenation of Benzene, Nitration of Benzene, Sulfonation of Benzene and Alkylation and Acylation of Benzene are some various chemical reactions of Benzene. Only about 5% of the product is 3-nitromethylbenzene. Having nitrogen present in a ring is very useful because it can be used as a directing group as well as a masked amino group. Organic Chemistry Animations Introduction, Acid Chloride Formation – Thionyl Chloride, Acid chloride formation-Phosphorus Pentachloride, Addition to C=O - loss of carbonyl oxygen, Molecules with a Plane of Symmetry – Feist’s Acid, Chiral Allenes Without Stereogenic Centres, Conformations of ethane – Newman projection, Conformational Analysis – Pea Moth Pheromone, Substrate structure controls substitution mechanism S, E2 Regioselective Elimination to Menthenes A, E2 Regioselective Elimination to Menthenes B, Formation of Diazonium Salt – Diazotization, Benzyne formation – Diazotization-decarboxylation, Enolisation and formation of syn aldol product, Enolisation and formation of anti aldol product, Simple Diastereoselectivity - cis gives syn aldol, Simple Diastereoselectivity - trans gives anti aldol, Conjugate Addition of MeSH to an Unsaturated Aldehyde, Conjugate Addition of Diethylamine to an Unsaturated Nitrile (Acrylonitrile), Conjugate Addition of Diethylamine to an Unsaturated Ester, Conjugate Addition of Enamine to Unsaturated Imine, Conjugate addition of peroxide to form epoxides, Regioselectivity 2-methoxybuta-1,3-diene and acrylonitrile, Regioselectivity 1,1-dimethylbutadiene and methyl acrylate, Stereochemistry of the dienophile - diesters, Stereochemistry of the dienophile - dinitrile, The Woodward Hoffman description of the Diels-Alder, Intramolecular Diels-Alder (E)-3-Methyldeca-1,3,9-triene, Intramolecular Diels-Alder – 1,3,9-decatrien-8-one, 2,3-Dimethylbutadiene and Acrolein(propenal), Quinone as Dienophile – Steroid Framework, Intramolecular Diels-Alder – Regioselectivity reversal, 8-Phenylmenthol auxiliary-controlled Diels-Alder, Paal-Knorr pyrrole synthesis via hemiaminal, Pyridine N-Oxide – Nucleophilic Substitution, Pyridine N-Oxide – Remote Oxidation And Rearrangement, 1,3-Dipolar Cycloaddition Isoxazole from nitrile oxide, Electrocyclic reactions are stereospecific, Conrotatory ring closure/opening - cyclobutene, Disrotatory ring closure/opening - hextriene, Semipinacol rearrangements of diazonium salts, Rearrangements with different nucleophiles, Retention of stereochemistry can indicate neighbouring group participation, Neighbouring group participation: alpha-lactone formation, Fragmentations are controlled by stereochemistry, Controlled by stereochemistry (Cis isomer), Controlled by stereochemistry (Trans – Less severe interactions), Controlled by stereochemistry (Trans – Severe interactions), Fragmentation of diastereoisomers (Trans-decalin I), Fragmentation of diastereoisomers (No ring fragmentation), Photolysis of diazomethane to produce a carbene, Methylation of carboxylic acid using diazomethane, Cyclopropanation of an Alkene by a Carbenoid, Stereoselective Aldol Reaction – Cis gives Syn, Stereoselective Aldol Reaction - Trans gives Anti, Endo-trig reactions (5-endo-trig orbital overlap), Hydroboration (Addition of boron hydride to alkenes), Pd-Carbonylative Kosugi-Migita-Stille Coupling Reaction, Pd-Butenolide Formation From Carbonylation Of A Vinyl Bromide, Pd-catalysed nucleophilic allylic substitution of functionalised compounds, Hydroboration of cyclopentadiene Ipc-borane, Acetylenic Ketone Reduction – Alpine Borane, Intermolecular aldol -proline – hydroxyacetone, BISCO Bismuth Strontium Calcium Copper Oxide – BSCCO, Chalcogenides, Intercalation Compounds and Metal-rich phases, Compare shape and size of 1s, 2s and 2p orbitals, Orbital-orbital Interactions and Symmetry Adapted Linear Combinations, Distortions of a octahedral complex with chelating ligands, Ligand Substitution Square Planar Complex, Possible morphologies of Au Nanoparticles, Electrophilic Addition Addition of bromine to an alkene, Electrophilic addition to alkenes – Symmetrical and Unsymmetrical, Nucleophilic Addition Addition of Hydride, Cyanohydrin Formation – Nucleophilic addition to the carbonyl group, Nucleophilic Substitution at Saturated Carbon, Nucleophilic Substitution Cyanide + Ethyl Bromide, Elimination – E2 Stereoselective for E alkenes, Radical Reactions Synthesis of Chloroalkanes, Radical Reactions CFCs and the Ozone Layer, Polyvinyl Chloride Poly(chloroethene) PVC, Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License. Res., 1971, 4, 240–248. This is followed by rapid loss of a proton to regenerate the aromaticity. Any cookies that may not be particularly necessary for the website to function and are used specifically to collect user personal data via analytics, ads, other embedded contents are termed as non-necessary cookies. Jmol.jmolLink(jmolApplet0,"select all;spacefill off; wireframe .1;","Sticks") Legal. Reaction type: Electrophilic Aromatic Substitution. Here's the general reaction for the nitration of benzene. But opting out of some of these cookies may have an effect on your browsing experience. Both aromatic and aliphatic compounds can be nitrated by different methods like heterolytic (nucleophilic and electrophilic) and radical nitrations. Learn more about the benzene reactions at vedantu.com. The mechanisms for these reactions are covered elsewhere on the site, and you will find links to these. Electrophilic Substitution Reaction Between Benzene And Nitric Acid Methyl groups are said to be 2,4-directing. While in organic nitrates, the nitrogen shares a bond with an oxygen atom which is bonded to a carbon atom. Notice that the new nitro group goes into the 3 position on the ring. The concentrated sulfuric acid is acting as a catalyst and so is not written into the equations. For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. Be the first to rate this page. 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