Bromobutane Post Lab

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SUNY Buffalo State College *

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213

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Chemistry

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Feb 20, 2024

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docx

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1. CHEMICAL EQUATIONS, MECHANISM 2. DATA:  Mass of n-butyl alcohol: 10mL  (10mL x 0.81 g/mL) = 8.1g  Moles of n-butyl alcohol: 8.1g x (1mol/ 74.121 g/mol) = 0.1093 moles (MW = 74.121 g/mol) (Density = 0.81 g/mL)  Mass of sodium bromide: 13.306g  Moles of sodium bromide: 13.306g x (1mol/ 102.894 g/mol) = 0.1293 moles (MW = 102.894 g/mol)  Volume of sulfuric acid: 11.5ml  (11.5ml x 1.83g/mL) = 21.05g  Moles of sulfuric acid: 21.05g x (1mol/ 98.079 g/mol) = 0.213moles (MW = 98.079 g/mol) (Density = 1.83g/mL)  Mass of purified product: 0.1237g

 Boiling point of product from distillation: 98 to 101 °C  FTIR of product–attach spectrum: 1-Bromobutane 3. RESULTS  Calculate the theoretical yield of 1-bromobutane: (1:1 ratio of 1-Butanol to 1- Bromobutane). (MW of 1-Bromobutane: 137.02 g/mol) (MW of 1-Butanol: 74.121 g/mol) Number of mol of 1-Butanol: 13.306g/ 137.02g/mol = 0.0971mol Theoretical Yield: 0.0971mol x 137.02g/mol = 13.31g  Calculate the % yield of purified 1-bromobutane: Actual Yield: 0.1237g  (0.1237g/ 13.31g) x 100 = 0.93% 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 band at 2,960.40 cm-1 reasons for the C-H bonds (the stretching vibrations), and the

bands around 740.30 cm-1 (range between 750-500 cm-1) accounts for the C-Br bond. Comparing to the known spectrum of the product, our product is accurate because all the bands compare to the known is present in our spectrum which is the reciprocal.  Did you produce the correct product? How do you know? What more could you do to identify the product and check its purity? Yes, we produced the correct product. We were able to tell by comparing our product FTIR with the original FTIR of 1-bromobutane, which resulted in a similar chemical property. We could also check its purity by regressing the infrared spectrum of a potentially contaminated sample on the reference spectrum of the pure substance. The resulting correlation coefficient would be the measure of the similarity between the two spectra.  Were there any problems encountered that might explain lower than expected yields or impure product? If so, discuss what happened. During our procedure, we did spill a significant amount of our product which is why our yield is much smaller. We tried to gather as much product as we can to continue, but more than half of the product was loss.

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 Provide a mechanism for the formation of the two main side products, dibutyl ether and 1-butene.  Why is it necessary to remove all water from 1-bromobutane prior to distillation? Because water can add extra weight making the yield bigger than what it actually is. Also, the high heat during the distillation can cause both water and bromobutane to react and form butanol.  To eliminate small amounts of pink bromine by-product, sodium bisulfite may be added to reduce it. Provide a balanced equation for the reaction of sodium bisulfite with

bromine.  How should the reaction conditions in this experiment be changed to produce 1- chlorobutane? We can replace sodium chloride with sodium bromide to increase the reaction time and temperature slightly. This will ensure that the compounds react and develop the desired product.