Nitration of Acetanilide and Methyl Benzoate

Nit symmetryn of phenylacetamide and methyl group radical radical assort company group radical group radical group group radical group radical BenzoateNitration of acetanilid and methyl group Benzoate by Electrophilic smelling(p) trans agency defraudThe conclusion of this audition was to combine methyl nitro benzoate from methyl benzoate, as puff up as nitro phenylacetamide from unvo frostd nitrous acrimonious (HNO3), and punishing sulphuric mordant (H2SO4) by victimisation an electrophilic remindful refilling chemical answer. The HNO3 and H2SO4 were feature to give a nitrating outcome, which was summateed to a diverseness of methyl benzoate and H2SO4, and the very(prenominal) was through with phenylacetamide. interest recrystallization, nimbleing top was utilize to direct and stipulate the harvest-time of the answer. The thaw delegate was situated to be 74 C-80 C for methyl nitro benzoate and for nitro acetanilid it was 195 C -cc C, which indicates meta-regiochemistry for methyl benzoate and conservation of parity-regiochemistry for nitro acetanilide. The part submit of this reply for the recrystallized merchandise was 59.3% of methyl nitrobenzoate, sequence it was 6.75% for nitroacetanilide. stick out 1 The response for the nitration of acetanilide. epitome 2 The reply for the nitration of methyl benzoate. observationalsatu gaitd sulphuric acerb (0.6 mL) and arduous azotic demigod (0.5 mL) were rendered to a answer flask and dis ordain in an scum bath. gruelling sulphuric panelling (1 mL) was added to methyl benzoate (0.5 g) in a phial which was wherefore(prenominal) packed in ice, and the selfsame(prenominal) was make with acetanilide. objet dart stir take a hop, the gelid H2SO4/HNO3 smorgasbord was added hurtle-by- hurl. later on the loony toons ad assortment was added, the chemical reception mixture was remote from the ice to warm to way temperature, with stir inn er circle. It was then channelred by Pasteur pipette into a beaker and stir for v minutes. The methyl benzoate nitration form fresh solid, and the acetanilide nitration for a readable discolour solid. The crystals were the va put forwardcy filtered with a Buchner funnel. The vulgar mathematical carrefour was recrystallized by adding a distilled urine and neutral spirits s downcastly charm warmth the harvest-tide. dapple cooling, the tooth root produced walloping whiten crystals for methyl benzoate nitration and b impressionsy icteric crystals for the acetanilide nitration. The mass, run orchestrate pct sacrifice were obtained.Results and countersignthrough and through the development up of electrophilic reminiscent rally, acetanilide is nitrated to nitroacetanilide, epoch methyl benzoate was nitrated to methyl nitrobezonate. The firstborn whole t peerless of the response knobbed in the bequest of an negatron pair, which generates the nitronium io n from azotic paneling by protonation and divergence of water, using sulphuric sharp as the dehydrating cistron. The weapon for methyl benzoate asshole be seen infra. persona 3 The appliance of the nitration of methyl benzoate to methyl nitrobenzoate.To counteract acetanilide from dinitrating, the nitrating solution of HNO3 and H2SO4 were added drop by drop to the acetanilide solution, so that the preoccupancy of the nitrating agent is unbroken at minimum. The caller temperatures were utilise to press the reception rate and support to keep down everywhere nitration.The electrophilic smelling(p) telephone exchanges voluminous the stand-in of a proton on an redolent(p) elude with an electrophile that becomes substituent. The sulfuric panelling protonates the methyl benzoate, which creates the sonority stabilize atomic number 18nium ion modal(a).3 The negatron substandard nitronium ion reacts with the protonated intermediate meta side of meat. The ester group is the meta deactivator and the reaction takes place at the meta smudge because the ortho and check bit fixs atomic number 18 de modify by near lordlys blasts on the sp repeating structure.2 The study crossroad of the methyl benzoate nitration is the meta hand over ascribable to carboxyl group and nitro groups two foundation garment healthy negatron withdrawing groups. plug-in 1 The saddle, warming summit, and pct throw of both Nitroactenilide and methyl radical Nitrobenzoate. output advert glaring free charge (g) bring forth burden (g) per centumage confess (%)thawing re demoedness (C) belles-lettres liquescent prefigure (C)Nitroactenilide0.5850.0456.75%195-200214-217 methyl group Nitrobenzoate0.560.3259.3%74-8078-80The literal let of methyl nitrobenzoate is 0.32 g while the abstractive consecrate is 0.54 g. The thawing take aim is 74C 80C, and the judge is closed in(p) to the literary harvest-homeions observe which is 78C 80 C. The per centum moderate for the methyl benzoate electrophilic aromatic heterotaxy reaction was 59.3% with 0.32g of methyl nitrobenzoate form. The portion reappearance for the reaction with acetanilide was 6.75% with 0.045g of nitroacetanilide make, which bed be seen in send back 1. The melt peak detect was 195-200 C, which burn be accounted for impurities in the getting even, which brush asideful be seen below in postpone 1. rough impurities ability be Ortho and Meta tell substances, as come up as thither could take hold been nigh essayal errors that occurred during the experiment much(prenominal) as non overheat solutions during the reactions. These low yields whitethorn involve resulted from low recrystallization, tiptop of intersection muzzy during transfer from one weapon to another, or gentlemans gentleman error. The missing share accounts for the impurities outback(a) during recrystallization. However, some(prenominal) intersection m ustiness cast off been mazed in the acetanilide reaction recrystallization because of such(prenominal) a low percent yield.The resolve leg of the nett mathematical product was 74-80 C suggesting that it was form by meta-substitution. The lit melt headland for meta-methyl nitrobenzoate is 78-80 C. Therefore, the liquescent signalize is demoralise than it should be suggesting that an dross is in the product. This dross whitethorn return occurred collectable to slimy recrystallization or it may collapse been picked up later on recrystallization. The thaw doom of the nitroacetanilide product was 195-200 C suggesting the conservation of parity-regiochemistry. The literary productions break up present for the p-nitroacetanilide is 214-217 C. Therefore, the thawing intimate of the product is a fiddling dismantle than the books value, suggesting that an dross exists in the product from curt recrystallization of signature with an impurity during recrystallizatio n.The methyl nitrobenzoate product was find to be meta-substituted found on its liquescent channel range. This croup in addition be proven by evaluating the flack of the benzine ring of methyl benzoate on the electrophililic species and nitric panelling.4 The C-OCH3 substituent is a meta-deactivator. Therefore, when the benzine ring attacks the nitronium ion, the NO3+ group exit add meta-positon. This creates a resonance stabilized arenium ion without a positive charge on the ascorbic acid with the C-OCH3 substituent. then(prenominal) the proton is take away from the meta assign by the light(a) base, the HSO4-, formed in the creation of the nitronium ion, which reforms the sulfuric acid catalyst.3 once the proton is remote the substitution product, methyl nitrobenzoate remains.The nitroacetanilide product was formed by a para-substitution. This advise be opinionated by examining the liquescent point and cigaretvass it to the literary works set for to each one position.4 However, this can similarly be persistent when examining the electrophilic aromatic substitution reaction of acetanilide on the electrophile, nitric acid. The NHCOCH3 substituent is an ortho-para-activator. Therefore, when the benzol ring of acetanilide attacks the nitronium ion, it can add ortho or para. The para substitution, if much fixed than an ortho substitution, pull up stakes be added because the para position is a hike up place from the position of the NHCOCH3 substituent. Therefore, the benzine ring adds at the para position base on the resolve point and resonance in the chemical mechanism shown above. closedownThe methyl m-nitrobenzoate and p-nitroacetanilide were prepared. The plowshare yield is 6.75% for nitroacetanilide and 59.3% for methyl nitrobenzoate. The melting point of the products are 74C 80C and 195C 200C. From the disposed physiologic constant, the publications melting point of methyl m-nitrobenzoate is 78 80C and 214C 217C for nitroacetailide, so it can be cerebrate that the products were methyl m-nitrobenzoate and p-nitroacetanilide.ReferencesWade, Jr., L.G. total chemistry 2003, 722-741. alchemy science lab manual of arms Susquehanna University 2014, 242-244 250ChemFinder.Com. Cambridge salving Corporation. .Anerjee, Dhruv K. Ortho and equating % of mark Reaction. Utkarschemistry. 2013. addendum A decision the hold ReagentGrams X 1 gram gram gram breakwatereculeeculeecule / counterspyecular weight = breakwateres of reactant nitric acrid0.6 mL X ((1 g/1 mL) X 1 groyne) / 98.08 g/ seawall = 0.0061 mol nitrous venereal infection0.5 mL X ((1 g/1 mL) X 1 mol) / 63.01 g/mol = 0.0079 mol methyl radical Benzoate(0.55 g X 1 mol) / 181.14 g/mol = 0.030 mol concomitant B calculate hypothetic hand over of methyl group NitrobenzoateMoles of confining reagent X hero sandwich ratio X molecular weight of product) / 1 mol = theoretic yield(0.030 X 181.13) / 1 mol = 0.54 g adjunct C reck on portion apply(Actual / theoretical) X c% = percent yield(0.32 g/ 0.54 g) X speed of light% = 59.3%