SYTHESIS OF CYCLOHEXENE

docx

School

Medaille College *

*We aren’t endorsed by this school

Course

301

Subject

Chemistry

Date

Feb 20, 2024

Type

docx

Pages

4

Uploaded by MegaThunderJackal10

Report
1. CHEMICAL EQUATIONS, MECHANISM 2. DATA Mass of cyclohexanol: 20.022g Moles of cyclohexanol: 20.022g x (1mol/ 100.158g/mol) = 0.200 moles (MW = 100.158 g/mol) Mass of phosphoric acid: 5mL (5mL x 1.685g/mL) = 8.43g Moles of phosphoric acid: 8.43g x (1mol/ 97.994 g/mol) = 0.086 moles (MW = 97.994 g/mol) (Density = 1.685g/mL) Cyclohexene Cyclohexanol
Mass of purified product: 5.14g Boiling point of product from distillation: 81 to 82 °C FTIR of product–attach spectrum: Cyclohexene 3. RESULTS Calculate the theoretical yield of cyclohexene: (MW of Cyclohexene: 82.143 g/mol) Theoretical Yield: 0.200mol x 82.143g/mol = 16.43g Calculate the % yield of purified cyclohexene: Actual Yield: 5.14g (5.14g/ 16.43g) x 100 = 31% 4. DISCUSSION/ QUESTIONS List and discuss at least 2 important bands from your FTIR and compare your spectrum to a known spectrum of the product. The C-H bond above the 3000cm-1 indicates that it has double bonds. The 3022.66 cm-1 indicates a C-H band. The little peaks circled in greens are the toluene that was still in present in the product. The band at 2900 cm-1 present an alkane C-H stretching, and the band at 1437.40 cm-1 shows a CH 2 bending. Our spectrum compared to the known spectrum is pretty accurate. The only difference is that the C=C stretching was not transferred enough in our spectrum.
^ (Known spectrum of Cyclohexene from google) ^ Did you produce the correct product? How do you know? What more could you do to identify the product and check its purity? Yes, the product we produce is the correct product. We could tell by comparing our spectrum with the known FTIR, which resulted in similar property with slight variations. We could identify the product and check its purity by determining the gas chromatographic analysis and a percent yield calculated of cyclohexene (chemical test). Is there any evidence of toluene, water, cyclohexanol, or any other impurity in your purified product in the IR? There is evidence of some toluene. The small peaks present in the IR (circled in green) are toluene. There might be other evidence of some impurities in the fingerprint area. Were there any problems encountered that might explain lower than expected yields or impure product? If so, discuss what happened. Though the percent yield of cyclohexene is low, the products of the experiment was achieved because cyclohexene was obtained by dehydrating cyclohexanol. The low percentage yield of cyclohexene could be due to the fact that some substances might have been behind in the flask and in the column during the distillations. What product(s) would be obtained by dehydration of 1-methylcyclohexanol and 2- butanol under similar reaction conditions? Dehydration of an alcohol gives a more stable alkene, more highly substituted as the major product. The major product obtained from 1-methylcyclohexanol gives two
Your preview ends here
Eager to read complete document? Join bartleby learn and gain access to the full version
  • Access to all documents
  • Unlimited textbook solutions
  • 24/7 expert homework help
isomeric alkenes (methylene cyclohexane and 1-methyl-1-cyclohexene). And the major products of 2-butanol are 2-butene (cis- and trans- isomers) and 1-butene. Why is it necessary to remove all water from the cyclohexene/toluene mixture prior to final distillation? Because any water present can interfere with the distillation, meaning water will co- distill or azeotrope and will not separate. Explain the purpose of the brine (saturated NaCl solution) washing step. The purpose of the brine is to remove large amounts of water than may be dissolved in the organic layer. It removes the bulk of water dissolved in the organic layer. Assign the peaks in the 1 H NMR spectrum to the specific hydrogens in cyclohexene The peak around 5.7ppm (vinylic region) correlates with Hydrogen 1 and 2, and hydrogens 3, 4, 9, and 10 associates with the 2ppm peak (allylic region, and hydrogen 5-8 correlates with 1.7ppm peak.