III.

Discussion & Conclusion As it is stated in the introduction section, in this lab cyclohexanone was produced by oxidation of cyclohexanol with sodium dichromate in the presence of a concentrated acid. The steps we performed in this lab was mixing proper ratios of cyclohexanol, sodium dichromate and concentrated sulfuric acid in a low temperature condition controlled by an ice-water bath followed by two times simple distillation to extract the produced cyclohexanone. In between the two distillation steps, organic solution, which contained cyclohexanone, was separated from the aqueous solution using a separatory funnel, and then the second distillation was performed on the organic layer to be able to obtain the produced cyclohexanone. As it is shown in the data sheet, after adding sodium dichromate the solution changed color from orange to dark brown and then dark green. However, the first distillation proceeds very slowly that we never got the chance to start the second distillation and obtain our own product. Therefore, I will be discussing the results from one of the classmates, which the GC and IR spectra are attached. The IR spectrum of cyclohexanol shows a relatively broad peak at around 3331.84-1, which could nicely be indicative of the O-H stretch in the cyclohexanol. Comparing this diagram with that of cyclohexanone, it could be discussed that the O-H stretch has been removed and instead a strong peak is detected around 17001. This peak could indicate that ketones present in the sample, and therefore this peak could be related to cyclohexanone, which was our desired product. However, there is a double peak at around 2800-3000-1 the presence of carboxylic acid (adipic acid), which is the by-products of the oxidation of cyclohexanol (below reaction). In the 3300-1 region, a very broad but weak peak is detectable, which could be related to some amount of alcohol (cyclohexanol) in the product. On the other hand, the attached GC diagram, indicates the presence of both cyclohexanone (first peak) and cyclohexanol (second peak). This diagram will be used to calculate the % yield using the area under each peak.

From the color change of the solution after addition of sodium dichromate, it can be concluded that a reaction has definitely occurred and the IR spectra of cyclohexanone with a peak related to ketones, and the GC results confirm the production of our product. However, since there are some peaks in the range of carboxylic acids, it could be concluded that the product is not 100% pure and is contaminated with adipic acid produced as a by-product. On the other hand, GC results showed peaks related to cyclohexanone and cyclohexanol and not any peak related to adipic acid appeared in this diagram. Therefore, it can be concluded that the amount of adipic acid in the mixture was very low, while there were still some cyclohexanol remained unreacted in the solution and affected the purity of our obtained product. Using the calculations shoed in the data sheet attached, the yield% of this reaction was calculated to be 97%. This is a relatively high yield, and

the reason why 100% yield has not been achieved could be the need for adding more of the oxidation agent (sodium dichromate/H+) to be able to use up all the cyclohexanol. IV. Questions 1. In this experiment, what is the purpose of the following; a. oxalic acid This chemical is added to the solution after the reaction to destroy the remaining dichromate. b. sodium chloride This chemical is added to the distillate containing cyclohexanone and aqueous layer to saturate the aqueous layer and thus salt-out cyclohexanone. c. anhydrous magnesium sulfate (or calcium chloride) This chemical is added to the separated organic solution to absorb any water remained and result a dry and pure organic solution. 2. What are the products of the Cr2O72-/H+ (excess) oxidation of the following compounds? State if no reaction occurs, state NR and the reasoning as to why. a. 2-methyl-2-butanol No reaction occurs. This is because this alcohol is a tertiary alcohol and therefore too bulky for the nucleophile to attack the acidic hydrogen connected to the oxygen. b. 3-methyl-2-butanol The product is 3-methyl-butanone. c. 3-methyl-1-butanol There may be two products: 3-methyl- butaneal and 3-methyl butanoic acid.