A explanation of cyclohexene, aqueous sodium hydroxide, and benzyl triethylammonium were used to synthesize 7,7 – dichloronorcarane by the forthcoming reboundion:
+ CHCl3 + OH - H2O + + Cl -
After quantity of the trial, the percent renovation was conducive to be 46. 21% Introduction The intention of this trial was to form 7,7-dichloronorcarane by instrument of carbene paraphernalia.
Cyclohexene, aqueous sodium hydroxide, and benzyl triethyl ammonium chloride were used to synthesize 7,7 – dichloronorcarane by the forthcoming reboundion:
+ CHCl3 + OH- H2O + + Cl-
In command to convey out this reboundion in a serious spell, a two-exhibition reboundion was used, avoiding the prolix requirements to convey out the trial as a single-exhibition reboundion, as well-mannered-mannered as the miss of ordinary works due to the nearness of introduce. The components of the two-stage reboundion were as follows: An radical exhibition containing the alkene and CHCl2; and an aqueous exhibition containing the worthiest OH.
Since the reboundants, CHCl2 and OH – would disjoined into divergent exhibitions, benzyl triethylammonium chloride was external as a exhibition-forward catalyst. Because the benzyl triethylammonium chloride has twain hydrophilic and hydrophobic properties, it could peevish the exhibition article and facilitated the enravishment of the hydroxide ion from the aqueous exhibition to the radical exhibition. Expected visionary veers in IR and 13C-NMR Procedure To originate, 0. 324g of cyclohexene was qualified delay 1 ml of 50% aqueous sodium hydroxide, 1ml of chloroform and 0. 040g of the exhibition forward catalyst benzyl triethylammonium chloride.
The reboundion was vivacious and heated at 40 degrees Celsius for an hour antecedently extracting the 7,7 dichloronorcarane through 2 methyl chloride parentage processes (1ml methylene chloride). The work was then air-dried until no more clear would exhale and weighed giving a percent renovation of 43%. The matter was then used to spend an IR and 13C-NMR spectra criterion giving the results. Results and Calculations Calculating moles of cyclohexene (81g cyclohexene/1ml) * (0. 40ml cyclohexene) = 0. 324g cyclohexene 0. 324g cyclohexene*(1mol cyclohexene/82. g cyclohexene) = 3. 95 * 10^-3 mol cyclohexene Calculating moles of chloroform 1. 49g/ml chloroform * 1ml of chloroform = 1. 49g of chloroform 1. 49g of chloroform * (1mol of chloroform/119. 4g chloroform)= 1. 25 * 10^-2 moles chloroform. Calculating moles of benzyl triethyl ammonium chloride (1. 08g benzyl triethylammonium chloride/ml) * 0. 040ml of benzyl triethylammonium chloride = 0. 0432 grams benzyl triethylammonium chloride * 1mol/227.
8g benzyl triethylammonium chloride = 1. 896 * 10^-4 moles benzyl triethylammonium chloride Finding the limiting reagent
CHCl3 +OH- H2O + Cl-
(balanced as-is delay a catalyst in rxn) 3. 95 * 10^-3 mol cyclohexene 1. 25 * 10^-2 moles chloroform 0. 058 moles of sodium hydroxide * Cyclohexane has the lowest quantity on the reboundant party and is the limiting reagent. Quantity of 7,7 dichloronorcarane= 3. 95*10^-3 moles * 165. 06g 7,7dichloronorcarane/mol= 0. 652g 7,7 dichloronorcarane hypothetical resign Experimental resign of dichloronorcarane= criterion tube delay – criterion tube delayout (27. 159grams – 26. 890grams)= 0. 269grams dichloronorcarane. Percent renovation (Actual body resign/ hypothetical body resign) * 100%= percent renovation (0. 69grams/0. 652grams) *100%= 41. 26% resign renovation Construction of 7,7 dichloronorcarane
+ CHCl3 + OH- H2O + Cl.
Discussion and Conclusions Discussion Topics and Questions
a. Compare IR and 13C-NMR spectra of cyclohexene and 7,7-dichloronorcarane and top out veers in IR vibrational frequencies and 13C-NMR resonances that living the structure of 7,7-dicholoronorcarane. Be unmistakable to standard the C-H reach of the cyclopropane ring hydrogens.
b. Why did you need to agitate the compromise vigorously during the reboundion? Since the reboundants are in divergent exhibitions, agitatering vigorously undisputed the catalyst to forward a hydroxide ion from the aqueous exhibition to the radical exhibition, allowing the reboundion to income as desired.
c. Why did you rinse the radical exhibition delay saturated sodium chloride explanation? Saturated sodium chloride was significant for the opposition of introduce. If the introduce was not removed from the explanation, it could rebound and form ordinary reboundions, such as those illustrative in Pavia: (4) (5)
d. Describe two chemical criterions and the visual results that would declare whether cyclohexene is bestow or lukewarm. Bromine in methylene chloride – If the individualization of bromide (red clear) results in a snowy explanation, cyclohexene is bestow. Potassium Permanganate (Baeyer criterion) – This reboundion depends on the speciousness veer from purple MnO4- ion into a brown submerge of MnO2.
e. Draw the structures of the works that you would anticipate from the reboundions of cis and trans-2-butene. Be unmistakable to expound on the stereochemistry of the works (enantiomers and meso forms).
f. Provide a means for the structure of the forthcoming works of a carbine individualization reboundion.