Oxidation of cyclododecanol to cyclododecanone

The determination from the oxidation condition of a carbon atom may be used to find a change in the oxidation state. The guidelines used give carbon a formal oxidation condition based on +1 for any atom less electronegative than co2, -1 intended for atoms even more electronegative, and 0 for C-C a genuine. The carbon must carry an oxidation process number that produces this amount equal absolutely no. Increasing the oxidation condition or oxidation number of the carbon atom is called a great oxidation effect. This is required for two ways: 1) Increasing the amount of carbon-O provides (or any more electronegative atom than C).

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2) Decrease number of C-H bonds.

Aldehydes and ketones can be synthesized by the oxidation of primary or secondary alcohols.

Conversation & Bottom line:

The initial part of this kind of experiment reviewed oxidation effect which was accustomed to synthesize ketone which is cyclododecanone from second alcohol known as cyclododecanol applying an oxidizing agent named sodium hypochloride. The second element of this experiment recrystallized the cyclododecanone simply by evaporate ether. Diethyl ether was likely to evaporate simply by letting it stay open immediately.

Seeing that time had not been enough, the ether was dried by simply air then recrystallized by simply pouring methanol on it. The solution was permit cool in ice drinking water then using vacuum purification to obtain the final product. Although the obtained product was light like powder, the identity of the merchandise couldn’t end up being confirmed while cyclododecanone but. Letting the obtained item stay open up on the view glass over night to make sure all methanol evaporated.

Following the third part was infrared spectroscopy and shedding point to define the obtained product. As a result of melting stage range of cyclododecanone, 57. 5ƒ -59. 3ƒ, compared to the literary works value (59-61ƒ) was close. Upon analysis of the attained infrared spectrum (credit to Kai Liu), it was found that not any signal appeared at 3580-3620 cm-1. This indicates that an “OH group not present in the merchandise. In addition , the IR spectroscopy result demonstrated that there is a signal appeared at 1709 cm-1, indicating the useful group ketone C=O present in the product therefore it can be stated that the received product was indeed natural cyclododecanol. The oxidation of cyclododecanol to cyclododecanone was successful.

The percent deliver of this test was 3. 78 %. This low produce is the consequence of losing item during the crystallization process. When ever adding the methanol to dissolve the crude item in the 60 ml Erlenmeyer flask then simply heated up. After staying dissolved, the mixture sitting at place temperature for approximately 5 minutes after which was submersed in an ice-water bath another 10 minutes to get crystallization to happen. But not most of crystal was obtained through vacuum filtration then allow it to dry naturally. The mass of pure cyclododecanone crystal was weighted and that value is less than it should be since some of the contaminated crystal was left inside the beaker with methanol and being removed. This oversight only could possibly be avoided with the addition of small amount of methanol and should possess waited much longer so more crystals could possibly be formed.

Job Cited

Gilbert, Steve and Sophie F. Matn. Experiment Organic Chemistry: A Miniscale & Microscale Procedure.

Belmont, CA: Thomson Brooks/Cole, 2010. 537-547. Print out

“Table of IRGI Absorption. The WebSpectra. UCLA Department of Chemistry and Biochemistry

22 Jun, 2000. Internet. 19 January, 2013.


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