The determination of the oxidation state of a carbon atom can be used to find a change in the oxidation state. The rules used assign carbon a formal oxidation state based on +1 for any atom less electronegative than carbon, -1 for atoms more electronegative, and 0 for C-C bonds. The carbon must bear an oxidation number that makes this sum equal zero. Increasing the oxidation state or oxidation number of the carbon atom is called an oxidation reaction. This is done in two ways: 1) Increasing the number of carbon-O bonds (or any more electronegative atom than C).
2) Decrease number of C-H bonds.
Aldehydes and ketones can be synthesized by the oxidation of primary or secondary alcohols.
Discussion & Conclusion:
The first part of this experiment examined oxidation reaction which was used to synthesize ketone which is cyclododecanone from secondary alcohol called cyclododecanol using an oxidizing agent called sodium hypochloride. The second part of this experiment recrystallized the cyclododecanone by evaporate ether. Diethyl ether was supposed to evaporate by letting it stay open overnight.
Since time wasn’t enough, the ether was dried by air and then recrystallized by pouring methanol on it. The solution was let cool in ice water then using vacuum filtration to obtain the final product. Although the obtained product was white like powder, the identity of the product couldn’t be confirmed as cyclododecanone yet. Letting the obtained product stay open on the watch glass overnight to make sure all methanol evaporated.
Following the third part was infrared spectroscopy and melting point to characterize the obtained product.
Due to the melting point range of cyclododecanone, 57.5℃ -59.3℃, compared to the literature value (59-61℃) was close. Upon analysis of the obtained infrared spectrum (credit to Kai Liu), it was found that no signal appeared at 3580-3620 cm-1. This indicates that an –OH group not present in the product. In addition, the IR spectroscopy result showed that there was a signal appeared at 1709 cm-1, indicating the functional group ketone C=O present in the product so it can be stated that the obtained product was indeed pure cyclododecanol. The oxidation of cyclododecanol to cyclododecanone was successful.
The percent yield of this experiment was 23.78 %. This low yield is the result of losing product during the crystallization process. When adding the methanol to dissolve the crude product in the 50 ml Erlenmeyer flask then heated it up. After being dissolved, the mixture sat at room temperature for about 5 minutes and then was submersed in an ice-water bath for another 10 minutes for crystallization to occur. But not much of crystal was obtained through vacuum filtration then let it dry naturally. The mass of pure cyclododecanone crystal was weighted and that value is less than it should be because some of the impure crystal was left in the beaker with methanol and being discarded. This mistake only could be avoided by adding small amount of methanol and should have waited longer so more crystals could be formed.
Work Cited
Gilbert, John and Stephen F. Martin. Experiment Organic Chemistry: A Miniscale & Microscale Approach.
Belmont, CA: Thomson Brooks/Cole, 2010. 537-547. Print
“Table of IR Absorption”. The WebSpectra. UCLA Department of Chemistry and Biochemistry,
22 Jun, 2000. Web. 19 Jan, 2013.
Remember! This is just a sample.
You can get a custom paper by one of our expert writers.
Get your custom essay
Helping students since 2015
Essay Writing Service Features
Our Experience
No matter how complex your assignment is, we can find the right professional for your specific task. Contact Essay is an essay writing company that hires only the smartest minds to help you with your projects. Our expertise allows us to provide students with high-quality academic writing, editing & proofreading services.
Free Features
Free revision policy
$10Free bibliography & reference
$8Free title page
$8Free formatting
$8How Our Essay Writing Service Works
First, you will need to complete an order form. It's not difficult but, in case there is anything you find not to be clear, you may always call us so that we can guide you through it. On the order form, you will need to include some basic information concerning your order: subject, topic, number of pages, etc. We also encourage our clients to upload any relevant information or sources that will help.
Complete the order form
Once we have all the information and instructions that we need, we select the most suitable writer for your assignment. While everything seems to be clear, the writer, who has complete knowledge of the subject, may need clarification from you. It is at that point that you would receive a call or email from us.
Writer’s assignment
As soon as the writer has finished, it will be delivered both to the website and to your email address so that you will not miss it. If your deadline is close at hand, we will place a call to you to make sure that you receive the paper on time.
Completing the order and download