Essay Chem Lab 2

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IR table:
Chemical Structure
Experimental Absorbance (cm-1)
Lit Absorbance
(cm-1)
Intensity
Functional groups/ Bonding

2929.40

2958.00

2872.19

1740.30
~2900

~2890

~2840

~1760
Weak

Weak

Weak

Moderate
Sp3 C-H Stretch
Sp3 C-H Stretch
Sp3 C-H Stretch
C=O carbonyl stretch

Discussion:
The objective of the experiment was to oxidize a secondary alcohol, isoborneol to ketone camphor. Secondary alcohols can be converted to ketones using very strong oxidizing agents such as chromic acid. In this experiment camphor was prepared by oxidizing a secondary alcohol, isoborneol. An environmentally friendly way to oxidize a secondary alcohol is by using bleach which contains 5.25% of sodium hypochlorite (1). Adding small amounts of acetic acid facilitates the reaction by converting sodium hypochlorite to hypochlorous acid (HOCl) (1). This is the active oxidizing agent. The mechanism was as fallows. (1)
Oxidation of isoborneol is an exothermic reaction, in order to avoid the creation of side product; the temperature should be controlled below 40 degrees Celsius (1). Enough sodium hypochlorite was added to ensure that reaction reached its completion. When hypochlorous acid (HOCl) is present in excess, a small portion can be transferred to starch and potassium iodide indicator paper and tested. The indicator paper should turn dark blue. Starch and potassium iodide will oxidize iodide ions to iodine (1). The reason this reaction was heated in this experiment was ensuring that the reaction went to completion, if enough energy was not supplied to the reactants the reaction would not go completely forward. This would leave traces of reactants in the final product (impurities) and consequently lower the yield (1). DCM was used to extract the camphor from the resulting solution because both camphor and DCM are non polar. This reaction works because like things dissolve in like things. This is why you cant you a polar compound like water. The camphor will stay in the layer with the DCM and you are better able to extract it that way. The organic layer was washed with a basic wash (NaHCO3) to remove unwanted acid impurities (3). This is used in this reaction because chronic acids are used to oxidize the isoborneol. This wash insures that the final product is pure. The IR for the final product showed a strong correlation with the IR that was found in the literature for camphor. This shows that the reaction was successful and the product that was formed in most likely pure. The main difference between the lit IR and the obtained IR was the experimental IR’s peaks were at slightly higher frequencies. However, this could be due to resonance. Therefore, the correlation between the two can still be considered strong. When comparing the experimental IR with the lit IR of isoborneol the mechanism can be shown. The alcohol in the isoborneol has been oxidized and is now showing up at the carbonyl peak in
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