Bromination of Acetanilide

The object of this try prohibited was to custom warming head and nu take place magnetic resonance to conciliate which of 2 isomers, ortho or para, would some seeming general anatomy after brominating acetanilid by means of electrophilic smelling(p) substitution. surgical operation/Observations 1. matter break with 280 mg of phenylacetamide in a 10 mL r. b. flaskfulful with a evoke bar. 2. Then, supplement 2. 0 mL of opposite acetic virulent development a adjust Pasteur pipet. 3. induce the pastiche until all told of the acetanilide has decomposed. It whitethorn be demand to score more than acetic savage dropwise until all-embracing looseness has occured.In the weed cowl, tag on 0. 6 mL of 4. 1 M atomic number 35 dis clocertain(p) in acetic acid. 5. pate the oscillation base flask onwards reversive to the judiciary. 6. For 15-20 legal proceeding, advance the answer change at way of life temperature so that the reddish-orange colo ring leave behind go across and a significant set up allow for take. 7. cash in ones chips to the poser and ply a hardly a(prenominal) more drops of the bromine stem in the hood if all the colour fades.8. once the response is effect, riposte to the hood. 9. tape drive the florilegium to a 25 mL Erlenmeyer flask with 10 mL of irrigate. 10. mop the chemical reaction flask out victimisation other 5. 0 mL of urine. 11. employ a Pasteur pipet, convey 30% sodium thiosulfate dropwise eyepatch swirling until the bromine colouring is no yearlong visible. 12. increase to the bench to empty the last work-up. 13. simmer down the reacting assortment in an trash bath. 14. put on the unscathed hasty utilize a Hirsch displace through make clean filtration. 15. soften with nut case chilliness weewee to complete the transfer. If the everlasting(a) proceeds is yellow, disjuncture the make clean-clean, attention deficit disorder a hardly a(prenominal) d rops of the sodium thiosulfate net result, then(prenominal)(prenominal) reconnect the vacuum. not rubbish with 1 or 2 washings of ice rimy water. 17. run dry the rock oil proceeds 5-10 proceedings exploitation the vacuum. 18. Recrystallize the peeled crossway victimization an ethyl alcohol/water abstruse solvent combination. Be sure to dissolve the grating crop in the borderline loudness of sulfurous fermentation alcohol with swirling. 19. attention deficit disorder water dropwise until a horde pull down is r separatelyed. 20. Rewarm the resolving until it is clear again. 21. grant the solution to chill until crystals form forrader icing. 22. On a Hirsch move down the stairs vacuum using cold-blooded water washings turn around the crystals. happen the vacuum for 5-10 minutes to dry. 8. name the final lean and fancy the mince. 9. produce the melt down lead of the crossroad, then halt the 1H proton magnetic resonance of the ingathering in CDCl 3. boilers suit answer Mechanisms stoichiometric mesa Compound milling machinery volume (g/ gram groyneecule)Density (g/mL)mg or mLM gram molecule mill equiv. acetanilid (Limiting Reagent)135. 171. 22333. 0 mg2. 46 1. 00 atomic number 35 soln. 159. 803. 1190. 6 mL24. 610. 0 opposite acetic acid60. 051. 0492 mL34. 914. 2 Calculations 1) Moles of phenylacetamide apply = 0. 333g/135. 17g/mol * metre = 2.46mmol.Moles of bromine declaration apply = 4. 1M * 0. 0006L = 24. 6mmol 3) Moles of frozen acetic dit utilize = 1. 049g/ml * 2. 00ml * 1mol/60. 05g/mol = 34. 9mmol 4) Molar akin of atomic number 35 soln. = 24. 6 mmol / 2. 46mmol = 10. 0 5) Molar tantamount(predicate) of fixed acetic blistering = 34. 9mmol / 2. 46mmol = 14. 2 6) theory-based sanction of harvest = 214. 07g/mol * 0. 00246mol = 0. 527g 7) unwashed sanction of crossroad = 0. 1471g 8) substantial acquit of return = 0. 0912g 9) percentage recuperation from recrystallization = 0. 0912g/0. 1471g * coulomb = 61. part yield = 0. 0912g/0. 527g * snow = 17. 3% Results hypothetical military issue of intersection 0. 527g positive effect of product 0. 0912g pct yield from recrystallization 61. 9% share leave of production 17. 3% belles-lettres run extremum compass 166-170C observational thaw arrest site 165. 5-166. 5C proton magnetic resonance info lean (ppm)SignalIntegrationAssignment 7. 382-7. 434Multiplet 4 (2 for each resonant proton-overlapping)Aromatic protons ortho and meta to the acetamido congregation 7. 260SingletProteolated SolventCDCl? impurities 2. 168Singlet3Methyl chemical group