Oxidation of Secondary Alcohol with Sodium Hypochlorite PDF

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Oxidation of Secondary Alcohol with Sodium Hypochlorite Results: Figure 1: IR Spectra of Unknown Alcohol C IR Report for "HOWDY" 105.0 90 80 3316.91

70

1139.48

788.59 844.23

1297.15

60 1449.99 1362.65

2853.69

%T 50 40

889.28 1255.50

2928.09 1024.80 966.47

30 1064.58

20 10 0.0 4000.0

3000

2000

1500

1000

650.0

cm-1

Figure 2: IR Spectra of Ketone Product Compared to IR Reference Spectra Date: Tuesday, July 14, 2020

IR Report for "HOWDY"

Time: 11:19 AM Central Daylight Time

105.0 90 80

864.12 908.13 1017.90 749.55

1052.08

1338.40

2862.62

70

1449.39

1310.92

2935.05

60

1118.36

1422.07 1221.12

%T 50 40 30 20

1705.59

10 0.0 4000.0

3000

2000

1500

1000

650.0

cm-1

IR Report for "HOWDY" 105.0 90 80

1052.08

1338.40

2862.62

70

1449.39

2935.05

749.55

1118.36

1422.07

60

864.12

908.13 1017.90

1310.92 1221.12

%T 50 40 30 20 1705.59

10 0.0 4000.0

3000

2000

1500 cm-1

&\FORKH[DQRQH

1000

650.0

Table 1: Properties of Unknown Alcohol C

Unknown Alcohol

Starting Mass (g)

Ketone Product BP (ºC)

Preweighted Vial Mass (g)

C

1.503

129-130

10.660

Ketone Product & Vial Mass (g) 11.527

Figure 3: Percent Yield Calculations of Ketone Product

Table 2: Structure and Boiling Point of Expected Ketone Products

Expected Ketone Cyclopentanone

Structure

Boiling point 131ºC

Cyclohexanone

155.6ºC

2-Heptanone

151ºC

3-Heptanone

146-149 ºC

Discussion and Conclusion: When looking at the IR spectra in figure 1 for our unknown alcohol C, we are able to determine that the unknown alcohol is cyclohexanol because of the different absorbances. One indicating absorbance is an -OH stretch at the 3300 mark. Another indicating absorbance is the CH stretch in the 2900 region. One last indicating absorbance is the -CO stretch n the 1000 region of the spectra. Based on these three absorbances, the unknown alcohol C is cyclohexanol. In addition to this, when looking at figure 2, we are comparing the IR spectra of our ketone product to the reference IR spectra of cyclohexanone. On indicating absorbance is the CO double bond stretch in the 1700 region. A second indicating absorbance is the -CH stretch at the 2900 region. When looking at the fingerprint region of the spectra, the absorbances are almost identical between the ketone product produced and the reference spectra of cyclohexanone. On the other hand, when looking at the boiling pint of the ketone product it is slightly lower than the actual boiling point of pure cyclohexanone. One reason for this could be that during the distillation process, the first distillate was collected too quickly or not completely, leaving the ketone product to be contaminated with dichloromethane. Although the boiling point was lower than pure cyclohexanone, I still conclude that the ketone product was cyclohexanone. Lastly, when looking at figure 3, we can see that our percent yield of ketone product was relatively high. Even though a good yield is considered to be above 70%, our yield is not low enough to be considered poor. Therefor the yield of our ketone product is okay. One reason for a lower yield of ketone product was during distillation, the dichloromethane was distilled too high and since we had to dump the first distillate, some ketone could have been dumped with it. In short, even though our %yield was not extremely high, it was a good yield considering the processes in the experiment. Sources of Error: One possible source of error in this experiment is during distillation. If the dichloromethane was distilled at too high of a temperature or too quickly, it could affect the amount of ketone product we had which would change our percent yield. Another possible source of error during the experiment is during the drying process of dichloromethane. if there was not enough potassium carbonate added then the dichloromethane would not be dried properly....