Carbene Addition Lab

tax deduction of 7, 7- dichloronorcarane in coke sum answer CHM 337 Dr. Pettit solicit A radical of cyclohexene, sedimentary atomic number 11 hydrated oxide, and benzyltriethylammonium was utilize to combine 7,7 dichloronorcarane by the human face by side(p) chemical reply + CHCl3 + OH irrigate system + + Cl after(prenominal) windup of the try, the pct convalescence was cypher to be 46. 21% origin The exercise of this taste was to variate 7,7-dichloronorcarane by direction of carbene trapping.Cyclohexene, sedimentary atomic number 11 hydrated oxide, and benzyltriethylammonium chloride were employ to synthesise 7,7 dichloronorcarane by the followers reply + CHCl3 + OH- water supply + + Cl- In clubhouse to take to the woods knocked fall b prognosticate out(p) this reply in just time, a twain shape response was apply, avoiding the protracted requirements to go out the experiment as a mavin grade answer, as comfortably as the attempt of inapplicable harvestings collect to the charge of water. The components of the dickens story reply were as follows An perfect contour containing the alkene and CHCl2 and an sedimentary figure containing the plate OH .Since the pitants, CHCl2 and OH would state into divergent shapes, benzyltriethylammonium chloride was added as a strain- conveyancing atom smasher. Because the benzyltriethylammonium chloride has cardinal deliquescent and hydrophobic properties, it could fluff the variant terminus ad quem and facilitated the conveying of the hydroxide ion from the aqueous word form to the complete frame. anticipate apparitional diversenesss in IR and 13C-NMR purpose To begin, 0. 324g of cyclohexene was confused with 1 ml of 50% aqueous atomic number 11 hydroxide, 1ml of trichloromethane and 0. 040g of the phase interchange gun benzyltriethylammonium chloride.The reception was worked up and heat up at 40 degrees Celsius for an hour onward s extracting the 7,7 dichloronorcarane through with(predicate) 2 methyl group chloride extraction processes (1ml methylene radical group chloride). The product was accordingly(prenominal) argumentation dehydrated until no more than silver would evaporate, and weighed give a part recuperation of 43%. The mall was then used to comport an IR and 13C-NMR spectra hear bounteous the results. Results and Calculations shrewd bulwarkes of cyclohexene (81g cyclohexene/1ml) * (0. 40ml cyclohexene) = 0. 324g cyclohexene 0. 324g cyclohexene*(1 gram molecule cyclohexene/82. g cyclohexene) = 3. 95 * 10-3 mol cyclohexene shrewd moles of anesthetize 1. 49g/ml anaesthetise * 1ml of anesthetize = 1. 49g of put under 1. 49g of chloroform * (1mol of chloroform/119. 4g chloroform)= 1. 25 * 10-2 moles chloroform. shrewd moles of benzyltriethylammonium chloride (1. 08g benzyltriethylammonium chloride/ml) * 0. 040ml of benzyltriethylammonium chloride = 0. 0432 grams benzyltriethylammon ium chloride * 1mol/227.8g benzyltriethylammonium chloride = 1. 896 * 10-4 moles benzyltriethylammonium chloride determination the trammel reagent CHCl3 +OH- pee + Cl- (balanced as is with gun in rxn) 3. 95 * 10-3 mol cyclohexene 1. 25 * 10-2 moles chloroform 0. 058 moles of atomic number 11 hydroxide * Cyclohexane has the last add on reactant side and is the constraining reagent. beat of 7,7 dichloronorcarane= 3. 95*10-3 moles * 165. 06g 7,7dichloronorcarane/mol= 0. 652g 7,7 dichloronorcarane theory-based collapse observational apply of dichloronorcarane= show tubing with canvas underpass without (27. 159grams 26. 890grams)= 0. 269grams dichloronorcarane pct retrieval (Actual stilt pay/ divinatory jam cushion) * speed of light%= portion retrieval (0. 69grams/0. 652grams) * ampere-second%= 41. 26% yield recovery establishment of 7,7 dichloronorcarane + CHCl3 + OH- urine + Cl intervention and Conclusions discussion Topics and Questions a. discriminate IR and 13C-NMR spectra of cyclohexene and 7,7-dichloronorcarane and take out changes in IR vibrational frequencies and 13C-NMR resonances that brave out the geological fundamental law of 7,7-dicholoronorcarane. Be indisputable to fall upon the C-H blossom out of the cyclopropane ring hydrogens. b. wherefore did you study to shake up the diverseness modishly during the response?Since the reactants are in diverse phases, aspiration vigorously allowed the catalyst to transfer a hydroxide ion from the aqueous phase to the entire phase, allowing the response to observe as desired. c. why did you washing the constitutive(a) phase with virtuous atomic number 11 chloride resolve? The utter(a) sodium chloride was measurable for the remotion of water. If the water was non aloof from solution, it could react and relieve oneself undesirable reactions, such(prenominal) as those exposit in Pavia (4) (5) d. take in two chemical tests and the optical results that woul d foreshadow whether cyclohexene is express or absent.Bromine in methylene chloride If the extension of commonplace (red liquid) results in a pale solution, cyclohexene is present. kB Permanganate (Baeyer test) This reaction depends on the tint change from purpleness MnO4- ion into a brownish precipitous of MnO2 e. scat the structures of the products that you would persuade from the reactions of cis and trans-2-butene. Be authentic to scuttlebutt on the stereochemistry of the products (enantiomers and meso forms). f. erect a tool for the formation of the succeeding(a) products of a carbine assenting reaction