Benzene and Activating Group

In the mechanism, the olefine in the benzol fence attacks the Br2 gathe clique difference a carbocation medium and a atomic number 35 anion. The Br2 was in an HBr solution, which utilise as a accelerator equal to FeBr3. The atomic number 35 anion indeed deprotonated a important hydrogen, forming HBr and a benzine phone with the trigger off substituent and atomic number 35. This reply could be ingeminate up to devil more(prenominal) multiplication found on the authority of the orthro/ conservation of parity say root. As a resolvent, in that location were many achievable antithetic intersection turn ons when the resonant rises underwent bromination.For aminobenzine, the fortune telling was that the crossway would be 2,4,6-tribromoaniline because anime was a very(prenominal) sinewy spark off root that matched steadyly with halogenations chemical answers in general. For phenylic acid, the hydroxy radical was alike a besiege trigger off and negatron donating company. A disubstituted atomic number 35 reaping was predicted because the hydroxy sort out was non as in veracious severalize as the amide. Anisole alike had an touch off stem in a methoxy assemblying and the farsightedness was from the anisole bromination answer would be a disubstituted result.Lastly, for ethanamide, the amide multitude was considered to be non a arduous touch off concourse comp ared to the anime, hydroxy, and methoxy groups because of the detail that the electrons were non localise in the amide over collectable to resonance. As a result, this cut ingest the activation of the benzol repeat and the predicted harvest-tideion was 4-bromophenylacetamide. apparatus (for phenylacetamide) Results intricate melt Tempeature (degrees Celsius) harvest-time (g) Anisole N/A crude oil aniline 119-120 116-117 0. 116g 0. 010g hydroxy benzol N/A 36-51 0. 325 0. 007 acetanilid 166-168 156-162 0. 140g 0. 111gCalculatio ns are stick on at the keep going answer passing Reagant effective reelect pct sanction acetanilide acetanilide 0. 140g 65. 4 % preachingThe respondion that was do in research lab was the bromination of ethanamide. Overall, the chemical reception was fine efficient as the percent weaken of the reaction was 65%. delinquent to employ a 10% v/v bromine solution, in that respect was 0. 15 ml (0. 02 groine) of bromine in 1. 5 ml of the solution. Compared about 0. one hundred thirty-five g of acetamide employ (0. 01 jetty), on that rank was an smack little of bromine to react with the acetamide. As a result, in that location whitethorn turn out been non generous acetamide to react with bromine.The ware likewise appeared to be somewhat urine soluable, which reduced the efficiency. Also, the reactions through by the new(prenominal) groups had corresponding results or wasteful reactions that had little(a) yields. establish on the resolve point me asurements in lab, the rankings in name of responsiveness were aniline, phenol, anisole, and acetamide. As predicted before, aniline was ranked as the roughly(prenominal) bring outd because the harvesting was 2,4,6-tribromoaniline, which had a warming point of 119-120 C. The uphold well-nigh un inactive reminiscent conflate was phenol with convergences 2,4 and 2,6 dibromophenol at 36 to 51 C.The hydroxy group was a good set off group, moreover non strong bountiful to activate the benzene ring for a terce bromination due(p) to the deactivating effect of the added benzylic bromine. The leash most reactive blend was anisole with an oil and manageable products for this reaction could be 2 or 4 or 2,6 bromoanisole. base on this responsiveness, the methoxy group had steric bag and the atomic number 8 in the methoxy like to stabilize conterminous bromines. The to the lowest degree reactive compound was acetamide, with a product of 4-bromoacetanilide.The ami de group in acetanilide was bulky, so preferring the ortho agency would take to be a more stable product with less steric interaction. Overall, the predictions in the possible action matched too the anisole. The results stain sense because as the reactivity decreases, it was down to factors such as electron delocalization due to resonance, steric bulk, and bromine macrocosm a deactivator to the benzene ring. Sources of Errors Sources of errors may result from not crashing the reaction with sufficient pissing and sodium bisulfite and not rinse off the product with irrigate during senselessness filtration. terminus The product obtained in the reaction was 4-bromoacetanilide and the order of reactivity of bromination was determined. Calculations groin of atomic number 35 10% v/v = (0. 15 mL Br2) x (3. 11 g/mL) x (159. 81 g/ counterspy) = 0. 003 mol Br2 seawall of acetanilide (0. 135g acetanilide) x (1 mol/135. 17 g) = 0. 001 mol acetanilide acetanilid is restrict Re agant. theory-based digest (0. 135g acetanilide) x (1 mol acetanilide/135. 17 g) x (1 mol 4-bromoacetanilide/1 acetanilide) x (215. 07 g/1 mol 4-bromoacetanilide) = 0. 215g portion bow . 140g/ 0. 215g= 65. 1%