Write The Mechanism Of Nitration Of Benzene

The heat of reaction, however, varies with the hydrocarbon to be nitrated. The first reaction is nitration of benzene to nitrobenzene. No solvent has been used (just nitric acid), and thus, the reaction. Write the equation for the steps involved in the mechanism of nitration of Benzene between Toluene and Nitrobenzene asked Jan 23 in Chemistry by Rubby01 ( 50k points) class-11. You can sort of. 3 Steps in Nitration of Benzene via Electrophilic Substitution Reaction Mechanism: 1: Production of the electrophile (the nitronium ion, NO 2 + ion) using conc. 3) Mechanism The first step is the formation of the NO. docx Page7 Nitration of Benzene Benzene will react with hot concentrated nitric acid to produce nitrobenzene. 515: Nitration procedure. The nitration of methyl benzoate, C6H8O2, undergoes such type of reaction with concentrated azotic acid and sulphuric acid to give methyl m-nitrobenzoate. Mechanism:— Mechanism of nitration of benzene is simple and two stepped. Activation and Deactivation. About Nitration of Benzene. I based that mostly on the analogy of nitration where nitration of salicylic acid with fuming HNO3 gives picric acid and the nitration of 3,5-dichlorosalicylic or 3,5-dibromosalicylic acids gives 2,4-dichloro-6-nitrophenol and 2,4-dibromo-6-nitrophenol correspondingly (see examples cited in Chem. A reaction between an organic compound and a nitrating agent leads to the introduction of a nitro group onto a carbon, nitrogen or oxygen atom of that organic compound []. Sulphonation 1. Created by. This organic chemistry video tutorial provides a basic introduction into the nitration of benzene mechanism which is one of the most common electrophilic aromatic substitution reaction. The Organic Chemistry Tutor 73,658. Rate of Nitration of Benzene with Mixed Acid R. Aromatic rings (also known as aromatic compounds or arenes) are hydrocarbons which contain benzene, or some other related ring structure. From the methyl benzoate, methyl m-nitrobenzoate will be formed and will undergo purification by re-crystallizing with methanol. ) than those of benzene or pyridine but they still fall in the aromatic rather than the alkene region. This is achieved by the formation of the nitronium ion by protonation of nitric acid from sulfuric acid. Benzene is heated with nitrating mixture to form nitrobenzene. The electrophilic reagent will attack the aromatic nucleus and the hydrogen atom of benzene is displaced by the electrophilic reagent. Write about Nitration of benzene. Nitration-In nitration , the attacking electrophilic species is nitronium ion NO 2 +. organic synthesis. BIGGS and R. 26 Introduction This method for the nitration of salicylic acid is a “green. Mechanism of Chlorination of Benzene: Step 1: formation of a chloronium ion. Officers Defence Academy - NDA Coaching for 10th, 12th 49,400 views 6:38. Nitration Characteristics. Mechanism of nitration of benzene Step 1. Paddington Academy (b) Benzene can be converted into amine U by the two-step synthesis shown below. Substitution of hydrogen of a benzene ring with a nitro group can only be done using nitronium ion or nitryl cation (NO 2 +) as an electrophile. The mixture is held at this temperature for about half an hour. Nitration of Benzene Mechanism - Electrophilic Aromatic Substitution Reactions - Duration: 5:31. This provides a better leaving group. Paddington Academy (b) Benzene can be converted into amine U by the two-step synthesis shown below. (Valerie(Burke(September(13,(2010((Abstract((( Thisproject(studied(the(electrophilic. The intermediate structures for the mechanism of this reaction are given below. Nitration of Benzene. Nitration of Methyl Benzoate BACKGROUND INFORMATION: Methyl benzoate is an aromatic compound structurally related to benzene. Adding a nitro group (NO2) to the benzene ring. 21 mL of methyl benzoate to the vial. As mentioned above, nitration simply means that we are adding a nitro group to an aromatic (or benzene) ring. Students should be able to outline the electrophilic substitution mechanisms of: nitration, including the generation of the nitronium ion and acylation using AlCl 3 as a catalyst. Learn more about the benzene reactions at vedantu. Our one step nitration procedure produces much higher yields without isolation of any intermediate. 2) Scheme NO 1. 9, pp 704-717. Draw the intermediates, starting materials, and products. The H2SO4 is a stronger acid than NO3 and it protonates it, yielding NO2+ (HSO4 + H20 as spectators). The mechanism for nitration of benzene: Step 1: Nitric acid accepts a proton from sulphuric acid and then dissociates to form nitronium ion. Nitration is a very important reaction as it adds a nitro- group to an aromatic ring. Nitration of Benzene. INTRODUCTION 1. Electrophilic Aromatic Substitution. (i) Give the reagents used to produce the electrophile for this reaction. The nitration process is highly exothermic, delivering more than 30 Kcal / mol to the medium. 1) Purpose The objective of this experiment is to synthesize the p‐bromonitrobenzene (bromo‐1‐nitro‐4‐benzene) out of bromobenzene, by nitration. In addition, to minimize secondary reaction, controlling the reaction temperature and relative reagent quantities are very important. Rate of Nitration of Benzene with Mixed Acid R. The nitration of nitrobenzene containing an electron-withdrawing -NO 2 group does not occur readily under the above conditions, in which use forcing conditions which requires the use of fuming nitric acid and concentrated sulphuric acid need to be employed. Step 2: Loss of the leaving group, a water molecule, to provide the nitronium ion, the reactive electrophile. 515: Nitration procedure. Paddington Academy (b) Benzene can be converted into amine U by the two-step synthesis shown below. Write about Nitration of benzene. Chlorine is an example of an ortho-para director and nitration of 1,4-dichlorobenzene produces 2,5-dichloronitrobenzene as its product. Hexadeuterobenzene is an isotope of benzene where all hydrogen atoms are replaced by deuterium. The heat of reaction, however, varies with the hydrocarbon to be nitrated. 3: Explain the reactions of acyl chlorides with nucleophiles in terms of an addition-elimination mechanism. Write an equation or equations to show the formation of this electrophile. Describe reaction mechanism. This is formed from nitric acid and sulfuric acid in the mechanism below. H 2 SO 4 and conc. Explain The Formation Of The Major And Minor Products. Nitration of paraffinic compounds • Gas phase reaction • Unlike aromatic compounds the paraffinic compounds are quite inert to nitrating agent. Write an equation/equations to explain the formation of NO 2 + from this mixture. Officers Defence Academy - NDA Coaching for 10th, 12th 49,400 views 6:38. Sulfonation of Benzene. Nitration is the most general process for the preparation of aromatic nitro compounds and it has played a great part in the development of theoretical organic chemistry. Label the transition states. The electrophilic substitution reaction between benzene and nitric acid. The nitration of methyl benzoate, C6H8O2, undergoes such type of reaction with concentrated nitric acid and sulfuric acid to yield methyl m-nitrobenzoate. Where go? How fast? Nitration of Toluene CH3 CH3 NO2 CH3 NO2 CH3 NO2 HNO3 63% 3% 34%. Now you first begin with The electrophilic substitution reaction between benzene and nitric acid. Stock FID 1 H-, 1 H{19 F}, 19 F-, 13 C-NMR EAS Nitration of fluorobenzene crude product (available for submission for credit, see laboratory. Loudon Chapter 16 Review: Chemistry of Benzene Jacquie Richardson, CU Boulder – Last updated 2/1/2019 3 Note that this regenerates the FeBr 3 catalyst and gives HBr as a waste product. Sc Entrance. Benzene ring is one of the components in most important natural products and other useful products. To achieve this, the nitration of bromobenzene was performed, followed by thin layer chromatography and column chromatography. As for example Benzene reacts with concentrated nitric acid in presence of concentrated sulphuric acid as a catalyst, and form nitrobenzene. The sulfuric acid was recovered and recycled by evaporating water, unreacted benzene and nitrobenzene by low pressure distillation. nitration of 1 4-dimethylbenzene gives a single product having the molecular formula c8h9n02 in high yield. The reaction follows the electrophilic substitution mechanism, and the mixture of concentrated sulfuric and nitric acid behaves as a nitrating agent. Nitration of Acetanilide and Methyl Benzoate by Electrophilic Aromatic Substitution Abstract. In this reaction, aldehydes are oxidized to carboxylic acids. Experimental Spectra: Reaction A (fluorobenzene) Stock fluorobenzene 1 H-, 1 H{19 F}, 19 F-, 13 C-NMR FID (FOR REFERENCE ONLY). This reaction is catalysed by aluminium chloride. Principle: Here nitration is occurring on nitrobenzene. It is the reaction between an organic compound and a nitrating agent (for example nitric acid ) that introduces a nitro group into the hydrocarbon producing an ester. organic molecule – in this case an alkyl benzene – to form a sulfur-carbon bond. From the methyl benzoate, methyl m-nitrobenzoate will be formed and will undergo purification by re-crystallizing with methyl alcohol. To get reaction on the pyridine ring, the N-oxide can be used as with pyridine itself. Write an equation or equations to show the formation of this electrophile. Explanation of mechanism: The electron-deficient CH 3 CO + electrophile ion is attacked by the delocalised pi electron system in the benzene ring breaking the aromaticity of benzene to form [C 6 H 6 COCH 3] +. The ipso aromatic electrophilic substitution of the carboxylic group. A model was proposed by Kekule in 1865: The resonance hybrid model explains these properties of benzene:. 4 Nitration •Nitration of benzene mechanism: •A nitro group can be reduced to form an amine •Combining these reactions gives a general process for installing an. This procedure has been adapted from the microscale procedure described in the third edition of. Use curly arrows to show the mechanism for the reaction between benzene and chlorine. • Anisole undergoes nitration about 10,000 times faster than benzene and about 400 times faster than toluene • This result seems curious because oxygen is a strongly electronegative group, yet it donates electron density to stabilize the transition state and the sigma complex. 136A 9 C-H distance 1. In second step aerenium ion loses proton to form niteobenzene. What is the nitrobenzene mechanism? Update Cancel. The nitration of a benzene ring is an electrophilic aromatic substitution reaction, andits general mechanism is summarized in Figure 2. Benzene, simplest organic, aromatic hydrocarbon and parent compound of numerous important aromatic compounds. First step consists of a. Name the mechanism involved and write an overall equation for the reaction. I based that mostly on the analogy of nitration where nitration of salicylic acid with fuming HNO3 gives picric acid and the nitration of 3,5-dichlorosalicylic or 3,5-dibromosalicylic acids gives 2,4-dichloro-6-nitrophenol and 2,4-dibromo-6-nitrophenol correspondingly (see examples cited in Chem. Write the equation for the steps involved in the mechanism of nitration of Benzene between Toluene and Nitrobenzene asked Jan 23 in Chemistry by Rubby01 ( 50k points) class-11. With the help of chemical equations, illustrate the steps involved in conversion of ethanamide, which is the following; (CH3CONH2) to ethanol nitrate (CH3CN. 7e: State the reagents used in the two-stage conversion of nitrobenzene to aniline. Mechanism of Nitration of Phenolsulphonic Acids Functional Derivatives of 5-Nitro-2-Furyl-Polyalkenes Über einige Nitroderivate des Pyridins The Kinetics of the Nitration of Quinoline and Isoquinoline Nitration of 8-Hydroxyquinoline with Dilute Nitric Acid and Nitrous Acid 97 Non-Aromatic Nitro Compounds. Now since the nitrogen atom has no lone pair to conjugate, it has no mesomeric effect on the ring, the but as nitrogen is now protonated, it has a high negative inductive effect. From the methyl benzoate, methyl m-nitrobenzoate will be formed and will undergo purification by re-crystallizing with methanol. class-12; Share It On Facebook Twitter Email. The electrophile attacks benzene ring to form an intermediate carbocation. Nitration of Benzene. This compound, shown below, can be prepared from methylbenzene by a sequence of nitration reactions. Choose A File 2. Phenol is more easily nitrated than benzene because of the presence of the hydroxyl group in phenol. A reaction profile for the nitration of benzene with nitronium ion has been successfully calculated for the first time. The Nitration of Methyl Benzoate O OMe HNO3, H2SO4 O OMe NO2 Procedure: 1. Sulfuric acid is the stronger acid and it protonates the nitric acid on the OH group so that a molecule of water can leave. The intermediate bezenonium ion is more stable when the OH is attached to it. Both π and σ transition states on the potential energy surface of the nitration of benzene with nitronium ion have been successfully optimized using unrestricted hybrid DFT procedure B3LYP with the triple-zeta 6-311G ** basis set without any. The Organic Chemistry Tutor 73,658. Draw the intermediates, starting materials, and products. Substitution of a nitro group into the aromatic ring is nitration. (1-5) Match a structure or term from the following list with each description below. The mechanism for nitration of benzene: Step 1: Nitric acid accepts a proton from sulphuric acid and then dissociates to form nitronium ion. As mentioned above, nitration simply means that we are adding a nitro group to an aromatic (or benzene) ring. If we increase the temperature there is a greater chance of entering more than one nitro group in the benzene ring. 104: acetic acid acetic anhydride acetonitrile acetyl nitrate acid in acetic alkyl anisole aqueous sulphuric acid aromatic compounds benzene benzyl catalysed cation chem chim chlorobenzene concentration of nitric conjugate acid diffusion dinitrogen pentoxide dinitrogen. You will use one of the starting materials below. Write an equation to show the formation of the reactive species. This forms water, which is a good leaving group. Write about Nitration of benzene. H 2 SO 4 and conc. Using Resonance Structures, Explain Why No Detectable Amount Of 3-nitrobromobenzene Is Found In The Product Mixture. Friedel Craft Acylation of Benzene with Mechanism for NEET ,B. Name of mechanism: Electrophilic substitution. EAS nitration mechanism. Product Distribution in the Nitration of Toluene. So if we started with a benzene ring, and we wanted to put a chlorine on our benzene ring, we would add some Cl2. Pyrrole undergoes electrophilic aromatic substitution preferentially at the 2 position as illustrated by the synthesis of 2-nitropyrrole. Write a mechanism for the nitration of methyl benzoate (major product only) Include formation of the electrophile from the reaction of nitric acid with sulfuric acid. Mechanism of Aromatic Nitration. Mechanism of benzene nitration and uses of benzene nitration; Nitration of other benzene compounds; Nitration. Sample 1 H-, 1 H{19 F}, 19 F-, 13 C-NMR EAS Nitration of fluorobenzene crude product (not available for submission for credit). The potential energy surfaces in gas phase and in aqueous solution for the nitration of benzene, chlorobenzene, and phenol have been elucidated with density functional theory at the M06-2X/6-311G(d,p) level combined with the polarizable continuum solvent model (PCM). there sulfuric acid is used as catalyst. The nitro. Klein, "Organic Chemistry", 2nd ed. Sulfonation takes place in concentrated acidic conditions and desulfonation is the mode of action in a dilute hot aqueous acid. Green Chem. Nitration is one of the most important examples of electrophilic substitution. 1 Representative Electrophilic Aromatic Substitution Reactions of Benzene HH EE ++ EE YY ++ HH YY δδ++ δδ–– 3. Step 1: formation of the electrophile, NO2+, from HNO3 and H2SO4 HNO3 + H2SO4 ® H2O + NO2+ + HSO4− Steps 2 and 3: substitution of NO2+ into the benzene ring Step 4: protonation of the HSO4− H+ + HSO4– ® H2SO4. Nitration of Benzene Aromatic Electroplilic Substitution Reaction compressed - Duration: 6:38. E) proceeds at the same rate as the nitration of benzene and yields predominantly the meta product. The nitration of a benzene ring is an electrophilic aromatic substitution reaction, andits general mechanism is summarized in Figure 2. Benzene is treated with a mixture of concentrated nitric acid and concentrated sulphuric acid at a temperature not exceeding 50°C. The most commonly encountered aromatic compound is benzene. Sc, AIIMS, DU, IIT, GATE(XL), M. I based that mostly on the analogy of nitration where nitration of salicylic acid with fuming HNO3 gives picric acid and the nitration of 3,5-dichlorosalicylic or 3,5-dibromosalicylic acids gives 2,4-dichloro-6-nitrophenol and 2,4-dibromo-6-nitrophenol correspondingly (see examples cited in Chem. In this reaction, the meta position is preferred. 18 and 19 2. a) To determine the melting point of m-nitrobenzoic acid compare with that of benzoic acid (literature value); and b) To differentiate between m-nitrobenzoic acid and benzoic acid using simple chemical tests. 21 mL of methyl benzoate to the vial. Electrophilic Aromatic Substitution (Aromatic compounds) Ar-H = aromatic compound 1. Nitration Converts benzene into nitrobenzene, C6H5NO2 The nitration of benzene is the first step in an historically important chain of reactions. Mechanism of nitration of benzene is simple and two stepped. The mechanism for the nitration of benzene works as follows: NO 2 + is attracted to the delocalised electrons in benzene. Aromatic Nitration. The nitration of a benzene ring is an electrophilic aromatic substitution reaction, andits general mechanism is summarized in Figure 2. • Anisole undergoes nitration about 10,000 times faster than benzene and about 400 times faster than toluene • This result seems curious because oxygen is a strongly electronegative group, yet it donates electron density to stabilize the transition state and the sigma complex. activating/deactivating). Hexadeuterobenzene is an isotope of benzene where all hydrogen atoms are replaced by deuterium. (i) Give the reagents used to produce the electrophile for this reaction. nitration of 1 4-dimethylbenzene gives a single product having the molecular formula c8h9n02 in high yield. Reactions can be of the ionic type or the free radical type. Nitration works the same way. Nitration of Benzene In contrast to nitration of alcohols, the nitration of benzene produces relatively stable nitro compounds that are much more difficult to detonate. Chapter 12Chapter 12 Reactions of Arenes:Reactions of Arenes: Electrophilic Aromatic SubstitutionElectrophilic Aromatic Substitution HH EE ++ EE YY ++ HH YY δδ++ δδ–– 2. The Organic Chemistry Tutor 73,658. Aromatic heterocycles 1: structures and reactions replace one CH group with a nitrogen atom NOT a chemical reaction! H benzene N. Be able to outline the completed electrophilic aromatic substitution reactions of the following types: halogenation, nitration, sulfonation, and Friedel-Crafts acylation & alkylation Sections: 15. Nitration-In nitration , the attacking electrophilic species is nitronium ion NO 2 +. General mechanism - Halogenation - The halogenation is catalysed by lewis acid like FeCl 3 or FeBr 3, AlCl 3 & ZnCl 2. Overall transformation : Ar-H to Ar-NO 2 Reagent : for benzene, HNO 3 in H 2 SO 4 / heat; Electrophilic species : the nitronium ion (i. 1 Criteria for Aromaticity* 15. Sulfonation of Benzene. Reactions can be of the ionic type or the free radical type. INTRODUCTION 1. Nitration development is a complex, lengthy and expensive process. Write the equation for the steps involved in the mechanism of nitration of Benzene between Toluene and Nitrobenzene asked Jan 23 in Chemistry by Rubby01 ( 50k points) class-11. Nitration of benzene to form nitrobenzene. nitric acid and conc. 3 Steps in Nitration of Benzene via Electrophilic Substitution Reaction Mechanism: 1: Production of the electrophile (the nitronium ion, NO 2 + ion) using conc. This video shows you the aromatic halogenation mechanism from the role of the Lewis Acid catalyst and formation of the super-electrophile, through the entire mechanism of adding halogen to benzene. WHITE University of Michigan, Ann Arbor, Michigan The rates of nitration of benzene by nitric acid in mixed acid to produce mononitroben- zene have been measured in well-emulsified reaction mixtures in the temperature range from 34’ to 54°C. Rate of Nitration of Benzene with Mixed Acid R. Use electron arrow pushing to show the formation of the electrophile (NO2 +), the intermediate arenium ion, and the final product of the reaction. Officers Defence Academy - NDA Coaching for 10th, 12th 49,400 views 6:38. NaBH4/CH3OH E. Resources to help you teach nitration of Benzene, in addition to an intro lesson on how to name Benzene derived compounds. c) benzoic acid. Examine The TLC Plate Below. Write equations of the following reactions: (i) Friedel-Crafts reaction-alkylation of anisole. The real structure is an intermediate of these structures represented by a resonance hybrid. Name of mechanism: Electrophilic substitution. Nitrated aromatic compounds have many uses in industry, particularly in explosives, drugs and medicines and dyestuffs. The carbocation then reacts with the π electron system of the benzene to form a nonaromatic carbocation that loses a proton to reestablish the aromaticity of the system. Similar reactions are: Sulphonation, Halogenation, Alkylation and Acylation. Write the mechanism of formation of nitronium ion, which is the electrophile of nitration, from nitric acid and sulfuric acid as catalyst. Ortho-para directing activators: nitration of phenol (or aniline) The carbocation intermediate from o- or p-addition can be stabilized by the substituent through resonance (See Fig. Nitration of Benzene We generate the highly electrophilic nitronium ion in situusing sulfuric acid to dehydrate nitric acid. INTRODUCTION 1. To achieve this, the nitration of bromobenzene was performed, followed by thin layer chromatography and column chromatography. The nitration process is highly exothermic, delivering more than 30 Kcal / mol to the medium. In case of an alkane, molecular formula of benzene must be the according to C n H 2n+2 i. Pyrroles Again acetyl nitrate has been used for the nitration of pyrrole33, to give mainly the 2-nitro derivatives (55%). Nitration of Acetanilide and Methyl Benzoate by Electrophilic Aromatic Substitution Abstract. Write the resonance structures of methyl benzoate that show that the CO, CH3 group is a deactivator at the o and p positions of the benzene ring, 4. b) benzene. The nitration of methyl benzoate, C6H8O2, undergoes such type of reaction with concentrated azotic acid and sulphuric acid to give methyl m-nitrobenzoate. 37: In which order should the reagents be used to convert benzene into phenylamine (aniline)? 17M. Sample 1 H-, 1 H{19 F}, 19 F-, 13 C-NMR EAS Nitration of fluorobenzene crude product (not available for submission for credit). Nitration of benzo[b]furan may be achieved with nitric acid in acetic acid and affords the 2-nitro compound, although nitrogen dioxide in benzene is reported to give the 3-nitro compound. From the methyl benzoate, methyl m-nitrobenzoate will be formed and will undergo purification by re-crystallizing with methanol. The mechanism for the nitration is that of an electrophilic aromatic substitution. Sulfonation of Benzene. The majority of organic nitration requires the use of sulfuric acid or oleum in the nitric acid because sulfuric acid is present as catalyst, solvent and dehydrating agent. Experiment 5 - Nitration of Methyl Benzoate is the active species that attacks the electron-rich aromatic ring in the first step of the mechanism of this reaction. Reactions can be of the ionic type or the free radical type. 4 ELECTROPHILIC AROMATIC SUBSTITUTION REACTIONS OF BENZENE 755 Step 2 Reaction of the benzene p electrons with the electrophile to form a carbocation inter- mediate. The electrophile is the nitronium ion, NO2+, which is formed at low. How Much Is The Refor Compound B? O 0. Created by Jay. E) proceeds at the same rate as the nitration of benzene and yields predominantly the meta product. b) benzene. Nitration is characterized by the introduction of the NO2 group intomolecule of an organic compound. , 40 (1947) 117–140). The bottom line: carboxylic acids are synthesized from aldehydes with the following combination of reagents:. The Organic Chemistry Tutor 73,658. A process for the nitration of aromatic compounds using nitric acid (65%) over zeolite beta has been applied to the synthesis of dinitro compounds [Catal. (4) OH NH 2 Step 1 Step 2. , 40 (1947) 117-140). Three reaction intermediates have been identified along both surfaces: the unoriented π-complex (I), the oriented reaction. nitric acid and conc. Coal-tar is the chief source of benzene. B) proceeds more rapidly than the nitration of benzene and yields predominantly the ortho, para products. Figure 2 Procedurei Nitration of Methyl Benzoate Tare a 5-mL conical vial and add 0. 1) The compound that is most reactive towards electrophilic nitration is: (IIT JEE 1985) a) toluene. For example, the high-explosive TNT (2,4,6-trinitrotoluene) is formed by triple nitration of toluene. Why is it important to maintain the reaction temperature low. The molecular formula of benzene is C6H6. Consider the nitration of benzene versus the nitration of trifluoromethylbenzene and toluene (methylbenzene). 10 A 12 C-H distance 2. Sulfonation SO3 + (CH2) 11 - CH3 CH 3- (CH2) 11 S – O H– + O O Sulfur Trioxide Alkyl Benzene Alkyl Benzene Sulfonic Acid. How many products will be formed? According to saytzeff rule how to decide which is the major product should I learn the reaction mechanism of nitration,sulphonation of haloarene for board? Is the given compound has center of symmetry and is it optically active ?. First the lone pair on the OH group of nitric acid. I performed this reaction by. Write the oxidation of the benzylic groups with C-H bond(s) to benzoic acid. The solvent effect on the geometries of stationary points and the reaction mechanism were systematically studied for the nitration of benzene with nitronium by self-consistent reaction field (SCRF) technique with different dielectric constants of 5. Electrophilic aromatic substitution is a method used when a functional group is needed to be substituted on to an aromatic compound. The carbocation then reacts with the π electron system of the benzene to form a nonaromatic carbocation that loses a proton to reestablish the aromaticity of the system. Procedure. 762 CHAPTER 16 • THE CHEMISTRY OF BENZENE AND ITS DERIVATIVES 16. Nitration(of(Substituted(Aromatic(Rings(and(Rate(Analysis(((Kayla(Diemoz(Dr. Created by Jay. ) Microscale Nitration of Methyl Benzoate B. Adding a nitro group (NO2) to the benzene ring. As in Benzene, double and single bond are alternated in the conjugated structure. [2] (d) The mechanism for the reaction is given below. Watch previous videos:- 1. Step 1: formation of the electrophile, NO2+, from HNO3 and H2SO4 HNO3 + H2SO4 ® H2O + NO2+ + HSO4− Steps 2 and 3: substitution of NO2+ into the benzene ring Step 4: protonation of the HSO4− H+ + HSO4- ® H2SO4. nitric acid and conc. However, this reaction proceeds slowly, which is inconvenient (dangerous) since hot, conc. These lead to the formation of dyes, and explosives. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. Introduction: In this experiment, you will do an aromatic nitration experiment. To get the benzene to react, we need to create an even stronger electrophile than the cationic nitrogen in nitric acid. 4k views · View 23 Upvoters. Sc Entrance. This video shows you the mechanism for the formation of. The nitration of anisole: A) proceeds more rapidly than the nitration of benzene and yields predominantly the meta product. How many products will be formed? According to saytzeff rule how to decide which is the major product should I learn the reaction mechanism of nitration,sulphonation of haloarene for board? Is the given compound has center of symmetry and is it optically active ?. , 2016, Advance Article DOI: 10. The potential energy surfaces in gas phase and in aqueous solution for the nitration of benzene, chlorobenzene, and phenol have been elucidated with density functional theory at the M06-2X/6-311G(d,p) level combined with the polarizable continuum solvent model (PCM). However, this reaction proceeds slowly, which is inconvenient (dangerous) since hot, conc. Typical Mechanism of Electrophilic Aromatic Substitution II. ) All electrophilic aromatic substitution reactions occur by similar mechanisms. It would be a good idea to write out the answer to the following problem to ensure that you understand the relationship of starting mate-rials to products in aromatic nitration before continuing to the next section. (a) The mechanism of the nitration of methylbenzene is an electrophilic substitution. Write the electron-pushing (arrow-pushing) mechanisms for the electrophilic aromatic substitution of benzene including halogenation, nitration, sulfonation, Friedel-Crafts alkylation, and Friedel-Crafts acylation. 21 mL of methyl benzoate to the vial. Anomalous Temperature For The Nitration Of Methyl Benzoate: reaction product Burning Questions on Phenol and Benzene. Nitrated aromatic compounds have many uses in industry, particularly in explosives, drugs and medicines and dyestuffs. of pharmaceutical intermediates; this is a broad area and so we can only skim the surface of this fascinating and diverse subject. The mechanism of Reaction 1 involves attack by an electrophile. Cautions: Nitrobenzene is readily absorbed into the skin, and the concentrated mineral acids are corrosive. Nitration of Acetanilide and Methyl Benzoate by Electrophilic Aromatic Substitution Abstract. Best answer. General Mechanism For Nitration Of Benzene. Electrophilic Substitution of Benzene. Nitration of Benzene Mechanism - Electrophilic Aromatic Substitution Reactions - Duration: 5:31. But when added concentrated sulfuric acid it. The Organic Chemistry Tutor 73,658. Define arene and aromatic Name aromatic compounds Describe the structure of. Nitration of Benzene. alkamonitor. Logic: Electrophilic nitration involves attack of nitronium ion on benzene ring. , 40 (1947) 117–140). Draw the intermediates, starting materials, and products. Label the transition states. In the first step, an intermediate is formed by nucleophilic attack of the benzene to the nitronium ion. Sulfonation takes place in concentrated acidic conditions and desulfonation is the mode of action in a dilute hot aqueous acid. So we start with the benzene ring, and we react benzene with a molecule that contains an electrophile in there. Step 2: The nitronium ion acts as an electrophile in the process which further reacts with benzene to form an arenium ion. Reaction conditions: AlX 3 + X 2 B. Nitration of benzene firstly involves the formation of a very powerful electrophile, the nitronium ion, which is linear. 10 A 12 C-H distance 2. (i) FeCl 3 polarises the Cl 2 molecule into oppositely charged ions & electrophilic attacking species Cl + is formed. D) proceeds more slowly than the nitration of benzene and yields predominantly the ortho, para products. 56 mL bromobenzene were used to complete the reaction. It is an electrophilic aromatic substitution in presence of NO 2, which is a strong electron withdrawing group and it directs the incoming substituents to the meta position. So if we started with a benzene ring, and we wanted to put a chlorine on our benzene ring, we would add some Cl2. 50 A 4 C-N distance 3. Name of mechanism: Electrophilic substitution. The reaction follows the electrophilic substitution mechanism, and the mixture of concentrated sulfuric and nitric acid behaves as a nitrating agent. If you want the nitration mechanism explained to you in detail, there is a link at the bottom of the page. Therefore, maximum electron density will be in toluene, followed by benzene and least in m-dinitrobenzene. 20 The following compound reacts with AlCl 3 followed by water to give a ketone A with the for- mula C 10H 10O. Chlorine is an example of an ortho-para director and nitration of 1,4-dichlorobenzene produces 2,5-dichloronitrobenzene as its product. When ortho-bromonitrobenzene is treated with sodium hydroxide at elevated temperature only one product is formed. Sulphonation 1. organic molecule – in this case an alkyl benzene – to form a sulfur-carbon bond. EAS nitration mechanism. Nitration is characterized by the introduction of the NO2 group intomolecule of an organic compound. Product Distribution in the Nitration of Toluene. Write the mechanism of formation of nitronium ion, which is the electrophile of nitration, from nitric acid and sulfuric acid as catalyst. Mechanism of benzene nitration and uses of benzene nitration; Nitration of other benzene compounds; Nitration. Draw the intermediates, starting materials, and products. Reactions can be of the ionic type or the free radical type. This occurs following the interaction of two strong acids, sulfuric and nitric acid. It is an electrophilic aromatic substitution in presence of NO 2, which is a strong electron withdrawing group and it directs the incoming substituents to the meta position. ) Let us first consider the reaction in a strong H2SO4 medium. In the second step, this intermediate is deprotonated by water and nitrobenzene is obtained. Hexadeuterobenzene is an isotope of benzene where all hydrogen atoms are replaced by deuterium. Draw the intermediates, starting materials, and products. The nitration of aromatic compounds can be represented by the eqn: ArH+HNO3=ArNO2+H2O Kinetics and Mechanism of Aromatic Nitration. The benzene of the reactant methyl benzoate is deactivated by an ester in the –COOCH 3 substituent, suggesting that the nitro group adds only to a meta position within the ring and forms methyl m-nitrobenzoate (see Figure 1). (iii) Name and outline the mechanism for this reaction, showing clearly the structure of C. The overall reaction is depicted in Figure 1. Write the oxidation of the benzylic groups with C-H bond(s) to benzoic acid. 1 Representative Electrophilic Aromatic Substitution Reactions of Benzene HH EE ++ EE YY ++ HH YY δδ++ δδ-- 3. Rate of Nitration of Benzene with Mixed Acid R. 1: Describe, using equations, the nitration, chlorination, alkylation, and acylation of benzene. 4e, pp 686-687. Why is it important that the nitration of benzene by nitric acid occurs in sulfuric acid? 4. Nitration of benzene to form nitrobenzene. Chapter 12Chapter 12 Reactions of Arenes:Reactions of Arenes: Electrophilic Aromatic SubstitutionElectrophilic Aromatic Substitution HH EE ++ EE YY ++ HH YY δδ++ δδ-- 2. characteristic of aromatic rings. WHITE University of Michigan, Ann Arbor, Michigan The rates of nitration of benzene by nitric acid in mixed acid to produce mononitroben- zene have been measured in well-emulsified reaction mixtures in the temperature range from 34' to 54°C. Best answer. In second step aerenium ion loses proton to form niteobenzene. Overall the reaction is written as: Nitration In this case, the generation of the electrophile is a little more complicated. Where go? How fast? Nitration of Toluene CH3 CH3 NO2 CH3 NO2 CH3 NO2 HNO3 63% 3% 34%. Hydroxylation. Among the following groups, which ones are o,p-directing? ED & 5 ave —OCH3 B) land 5 C) 2 and 4. Nitration of Benzene Aromatic Electroplilic Substitution Reaction compressed - Duration: 6:38. This page looks at the facts about the nitration of benzene and methylbenzene. draw this Posted 8 years ago Nitration of1,4-dimethylbenzene (p-xylene)gives asingle product having themolecular formula C8H9NO2. The reaction is much faster if it is carried out by heating benzene with a mixture of concentrated nitric acid and concentrated sulfuric acid. Links to Existing Calendars. The electrophilic reagent will attack the aromatic nucleus and the hydrogen atom of benzene is displaced by the electrophilic reagent. Calculations described herein were performed using Chem CAChe. The electrophile is the nitronium ion, NO2+, which is formed at low. Friedel Craft Acylation of Benzene with Mechanism for NEET ,B. If we use the nitration of benzene as a reference, we can assign the rate of reaction at one of the carbons to be 1. This compound, shown below, can be prepared from methylbenzene by a sequence of nitration reactions. MECHANISM FOR NITRATION OF BENZENE Step 1: An acid / base reaction. Adding a nitro group (NO2) to the benzene ring. However, oxidants and oxidative damage have not been well characterised in IBD mucosa. This section. The nitration process is highly exothermic, delivering more than 30 Kcal / mol to the medium. NaBH4/CH3OH E. Overall transformation : Ar-H to Ar-SO 3 H, a sulfonic acid. 1 Lesson 3- Nitration and Halogentation of Benzene A lesson explaining the nitration and halogenation reactions of benzene. Nitration is the most general process for the preparation of aromatic nitro compounds and it has played a great part in the development of theoretical organic chemistry. Why is it important to maintain the reaction temperature low. Benzene reacts with ethanoyl chloride in a substitution reaction to form C 6 H 5 COCH 3. Nitration of benzene firstly involves the formation of a very powerful electrophile, the nitronium ion, which is linear. • Parrafins can be attacked by certain atoms and free radicals. Be sure to show the mechanism. 10 A 5 C-N distance 2. Nitration of benzene to form nitrobenzene. Nitration of bromobenzene (n°28) 1. Konovalov in 1888. I based that mostly on the analogy of nitration where nitration of salicylic acid with fuming HNO3 gives picric acid and the nitration of 3,5-dichlorosalicylic or 3,5-dibromosalicylic acids gives 2,4-dichloro-6-nitrophenol and 2,4-dibromo-6-nitrophenol correspondingly (see examples cited in Chem. Nitration Converts benzene into nitrobenzene, C6H5NO2 The nitration of benzene is the first step in an historically important chain of reactions. You will use one of the starting materials below. Useful as a selective and mild nitration method-for example, allowing. Adding a nitro group (NO2) to the benzene ring. Write an equation or equations to show the formation of this electrophile. Give the reagents used to produce the electrophile needed in Reaction 1. Recognize and be able to write the mechanism of electrophilic aromatic substitution 4. The overall reaction for the nitration of methyl benzoate. The process is one example of electrophilic aromatic substitution, which involves the attack by the electron-rich benzene ring: Alternative mechanisms have also been proposed, including one involving single electron transfer (SET). Learn more about the benzene reactions at vedantu. Click to enlarge. Benzene is treated with a mixture of concentrated nitric acid and concentrated sulphuric acid at a temperature not exceeding 50°C. Nitration of benzo[b]furan may be achieved with nitric acid in acetic acid and affords the 2-nitro compound, although nitrogen dioxide in benzene is reported to give the 3-nitro compound. (a) The mechanism of the nitration of methylbenzene is an electrophilic substitution. It is aromatic electrophilic substitution reaction. This occurs following the interaction of two strong acids, sulfuric and nitric acid. The nitration process is highly exothermic, delivering more than 30 Kcal / mol to the medium. And so that's the mechanism for the bromination of benzene. CHEM 322L Experiment 7: Nitration of Methyl Benzoate 1. Sc Entrance. Write the resonance structures of methyl benzoate that show that the CO, CH3 group is a deactivator at the o and p positions of the benzene ring, 4. This is an electron withdrawing deactivating group. This compound, shown below, can be prepared from methylbenzene by a sequence of nitration reactions. I based that mostly on the analogy of nitration where nitration of salicylic acid with fuming HNO3 gives picric acid and the nitration of 3,5-dichlorosalicylic or 3,5-dibromosalicylic acids gives 2,4-dichloro-6-nitrophenol and 2,4-dibromo-6-nitrophenol correspondingly (see examples cited in Chem. 1 mole of sulfuric acid is required per nitration. 15 & 16) C6H6 is an unusually stable molecule that does NOT react like alkenes do. And so that's the mechanism for the bromination of benzene. Inner-sphere electron transfer in organic chemistry. Write equations of the following reactions: (i) Friedel-Crafts reaction-alkylation of anisole. Nitration of Benzene Benzene reacts with nitric acid at 323-333k in presence of sulphuric acid to form nitrobenzene. In addition to exerting an effect on the speed of reaction, substituents on the benzene ring also influence the regiochemistry of the reaction. 71 relative to the rate of nitration of benzene (51). Write the electron-pushing (arrow-pushing) mechanisms for the electrophilic aromatic substitution of benzene including halogenation, nitration, sulfonation, Friedel-Crafts alkylation, and Friedel-Crafts acylation. Flashcards. Watch previous videos:- 1. Activation and Deactivation. This type of nitration. (a) The mechanism of the nitration of methylbenzene is an electrophilic substitution. A process for the nitration of aromatic compounds using nitric acid (65%) over zeolite beta has been applied to the synthesis of dinitro compounds [Catal. Therefore, when nitrobenzene is formed, the second nitration reaction goes much slower than the first due to a deficient amount of electrons for the nucleophilic attack. Coal-tar is the chief source of benzene. 摘要: Both π and σ. Sulfonation SO3 + (CH2) 11 - CH3 CH 3- (CH2) 11 S – O H– + O O Sulfur Trioxide Alkyl Benzene Alkyl Benzene Sulfonic Acid. 1) Purpose The objective of this experiment is to synthesize the p‐bromonitrobenzene (bromo‐1‐nitro‐4‐benzene) out of bromobenzene, by nitration. 37: In which order should the reagents be used to convert benzene into phenylamine (aniline)? 17M. (1-5) Match a structure or term from the following list with each description below. The reaction follows the electrophilic substitution mechanism, and the mixture of concentrated sulfuric and nitric acid behaves as a nitrating agent. 515: Nitration procedure. Name and outline the mechanism for the reaction with NaBH 4 in Reaction 2. That is, they control where the new substituent appears in the product. Sulfonation of benzene is a process of heating benzene with fuming sulphuric acid (H 2 SO 4 +SO 3) to produce benzenesulfonic acid. Label the transition states. we Know benzene can be nitrated, but here, I`ll tell you what, Why don`t you give us the Unbalanced equation, and then we`ll work on Balancing it can`t say fairer than that! 0. Where go? How fast? Nitration of Toluene CH3 CH3 NO2 CH3 NO2 CH3 NO2 HNO3 63% 3% 34%. Organic Chemistry II Sample Problems and Solutions: Chap 16. First step consists of a. If you want the nitration mechanism explained to you in detail, there is a link at the bottom of the page. This video shows you the aromatic halogenation mechanism from the role of the Lewis Acid catalyst and formation of the super-electrophile, through the entire mechanism of adding halogen to benzene. Write the mechanism for the nitration of nitrobenzene. Alone, nitric acid is not a strong enough electrophile to react with bromobenzene. Principle: Here nitration is occurring on nitrobenzene. Sulfonation of Benzene. If we use the nitration of benzene as a reference, we can assign the rate of reaction at one of the carbons to be 1. Created by Jay. 01 mL of nitric acid, 4. The mechanism of Reaction 1 involves attack by an electrophile. Friedel Craft Acylation of Benzene with Mechanism for NEET ,B. Nitration of Benzene Aromatic Electroplilic Substitution Reaction compressed - Duration: 6:38. nitric acid is a powerful oxidizer, and organic compounds are easily oxidizable. In the first step, an intermediate is formed by nucleophilic attack of the benzene to the nitronium ion. Step 1: formation of the electrophile, NO2+, from HNO3 and H2SO4 HNO3 + H2SO4 ® H2O + NO2+ + HSO4− Steps 2 and 3: substitution of NO2+ into the benzene ring Step 4: protonation of the HSO4− H+ + HSO4– ® H2SO4. org/archive/rhodium/chemistry/nitrobenzene. Which combination of reagents used in the indicated order with benzene will give m-nitropropylbenzene? a) 1) HNO 3 /H 2 SO 4 , 2) CH 3 CH 2 CH 2 Cl/AlCl 3 b) 1) CH 3 CH 2 CH 2 Cl/AlCl 3 , 2) HNO 3 /H 2 SO 4. The kinetics and yields of the two products from 1-chloro-2,4-dinitrobenzene under a variety of conditions are reported and discussed in relation to a previously proposed mechanism. This is formed from nitric acid and sulfuric acid in the mechanism below. Label the transition states. Watch previous videos:- 1. 3 Steps in Nitration of Benzene via Electrophilic Substitution Reaction Mechanism: 1: Production of the electrophile (the nitronium ion, NO 2 + ion) using conc. I based that mostly on the analogy of nitration where nitration of salicylic acid with fuming HNO3 gives picric acid and the nitration of 3,5-dichlorosalicylic or 3,5-dibromosalicylic acids gives 2,4-dichloro-6-nitrophenol and 2,4-dibromo-6-nitrophenol correspondingly (see examples cited in Chem. The mechanism for the nitration is that of an electrophilic aromatic substitution. Being the stronger acid, sulfuric acid protonates nitric acid, with. We can write, in general ana= d ()2 where n is the number of microphase domains per unit volume of the solution and ad is the area of a single domain. HNO 3 and it is found nitro-benzene. 1039/C5GC02747K. Sulfonation of Benzene. No solvent has been used (just nitric acid), and thus, the reaction. Want to learn while you write? This app has 5 powerful features to help improve your writing and build confidence. Nitration of Methyl Benzoate Benzene and somewhat less reactive aromatic compounds such as methyl benzoate can be nitrated with a mixture of nitric and sulfuric acids that ionizes completely to generate the nitronium and hydronium ions: HNO 3 + 2H 2SO 4 NO 2 + + 2HSO 4-+ H 3O + Hot concentrated nitric acid is also a good oxidizing agent. A process for the nitration of aromatic compounds using nitric acid (65%) over zeolite beta has been applied to the synthesis of dinitro compounds [Catal. In this experiment, acetanilide produced ortho and para mono nitroacetanilides; the nitronium ion (formed from the reaction between concentrated nitric acid and sulfuric acid), is directed to the ortho and para positions by the -NHCOCH3 group attached to the. This is identi. To get the benzene to react, we need to create an even stronger electrophile than the cationic nitrogen in nitric acid. Write an equation to show the formation of the reactive species. From the methyl benzoate, methyl m-nitrobenzoate will be formed and will undergo purification by re-crystallizing with methanol. Nitric acid and nitronium ion. It is the process by which binding of the nitro group (NO is made 2 ) to a atom of carbon , which generally effect substitution atom hydrogen. The benzene of the reactant methyl benzoate is deactivated by an ester in the –COOCH 3 substituent, suggesting that the nitro group adds only to a meta position within the ring and forms methyl m-nitrobenzoate (see Figure 1). In this section, reactions of benzene are discussed to illustrate electrophilic substitution reactions of arenes. YConcepts for Chapter 19: Aromatics II: Reactions of Benzene and Its Derivatives I. Officers Defence Academy - NDA Coaching for 10th, 12th 49,400 views 6:38. Nitration of Acetanilide and Methyl Benzoate by Electrophilic Aromatic Substitution Abstract. Introduction: In this experiment, you will do an aromatic nitration experiment. The electrophile is the nitronium ion, NO2+, which is formed at low. Kindly refer to the following link: https://www. Electrophilic Aromatic Substitution. (i) Give the reagents used to produce the electrophile for this reaction. Electrophilic. The usual structural representation for benzene is a six carbon ring (represented by a hexagon) which includes three double bonds. 2: Describe and explain the mechanism for the nitration, chlorination, alkylation, and acylation of benzene. What is the difference between Electrophilic and Nucleophilic Substitution? Mechanism of Electrophilic and Nucleophilic Substitution. The process is one example of electrophilic aromatic substitution, which involves the attack by the electron-rich benzene ring: Alternative mechanisms have also been proposed, including one involving single electron transfer (SET). In this experiment, you will do an aromatic nitration experiment. Formation of carbonium ion:. Nitration of toluene gives benzidine, aniline, aminosalicylic acid, phenylenediamine. The nitration of methyl benzoate is carried out using a mixture of sulfuric and. HOO S OOH; methyl m. You may use benzene andtoluene as your aromatic…. Its main use is in the manufacture of precursors to polyurethane and other industrial chemicals. Notes to the Instructor: This experiment is suitable for an advanced project in the full year organic laboratory or as a project in an upper level organic course. These temperatures are not high enough for…. Because the nitronium ion is a good electrophile, it is attacked by benzene to produce Nitrobenzene. Nitration is carried out under reflux at 50oC using a nitrating mixture. quinolines of various structures. The reaction follows the electrophilic substitution mechanism, and the mixture of concentrated sulfuric and nitric acid behaves as a nitrating agent. The rate of nitration of (chloromethyl)benzene, CH 2Cl, is 0. (a)4-Nitromethylbenzene can be formed by the nitration of methylbenzene. Label the transition states. , 40 (1947) 117-140). q The detailed mechanism of the nitration of benzene with mixed acid is given below: q The usual "two-step mechanism" for aromatic substitution is represented in steps 3 and 4, with the "attack step" being rate determining. In this reaction, the meta position is preferred. Now since the nitrogen atom has no lone pair to conjugate, it has no mesomeric effect on the ring, the but as nitrogen is now protonated, it has a high negative inductive effect. Electrophilic aromatic substitution is a method used when a functional group is needed to be substituted on to an aromatic compound. Explain The Formation Of The Major And Minor Products. Which combination of reagents used in the indicated order with benzene will give m-nitropropylbenzene? a) 1) HNO 3 /H 2 SO 4 , 2) CH 3 CH 2 CH 2 Cl/AlCl 3 b) 1) CH 3 CH 2 CH 2 Cl/AlCl 3 , 2) HNO 3 /H 2 SO 4. Dilute nitric acid (0. The nitration process is highly exothermic, delivering more than 30 Kcal / mol to the medium. The reaction mechanism is beyond the scope of undergraduate organic chemistry courses. Nitration of benzene to form nitrobenzene. since nitration is an electrophilic aromatic substitution reaction it is affected by the other substituents on the benzene ring. The nitration mechanism depends on the reagents and the operating conditions. Write an equation or equations to show the formation of this electrophile. Watch previous videos:- 1. The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. An example of a hydroxylation reaction catalyzed through a biological pathway is the hydroxylation of p-hydroxyphenylacetate using the enzyme p-hydroxyphenylacetate-3-hydroxylase to produce 3,4-dihydroxyphenylacetate. Pyrrole is also more reactive towards electrophiles than benzene or 1148 43. Chlorine is an example of an ortho-para director and nitration of 1,4-dichlorobenzene produces 2,5-dichloronitrobenzene as its product. Nitration of toluene gives benzidine, aniline, aminosalicylic acid, phenylenediamine. Subsequently, a σreactant-complex and a σ intermediate (Wheland intermediate) were located by the intrinsic reaction coordinate (IRC. draw this Posted 8 years ago Nitration of1,4-dimethylbenzene (p-xylene)gives asingle product having themolecular formula C8H9NO2. Explain the mechanism for the nitration of benzene, using curly arrows to show the movement of electron pairs. Sc, AIIMS, DU, IIT, GATE(XL), M. Formation of arenium ion. Pyrroles Again acetyl nitrate has been used for the nitration of pyrrole33, to give mainly the 2-nitro derivatives (55%). The electrophilic. In the case of benzene, the hybrid structure is the one below (the one you learn at school):. Nitration of benzene firstly involves the formation of a very powerful electrophile, the nitronium ion, which is linear. The heat of reaction, however, varies with the hydrocarbon to be nitrated. INTRODUCTION 1. donated to the electrophile. Write The Detailed Mechanism Of The Nitration Of Bromobenzene.