Oxidation of Cyclododecanol to Cyclododecanone

Topics: Alcohol, Redox, Chemistry Pages: 3 (708 words) Published: February 9, 2013
Cam-Ha Nguyen
Abstract: Using hypochlorous acid to convert secondary alcohol called cyclododecanol to the corresponding ketone which is cyclododecanone by oxidation.
Gilbert, John and Stephen F. Martin. Experiment Organic Chemistry: A Miniscale & Microscale Approach. Belmont, CA: Thomson Brooks/Cole, 2010. 537-547. Print.
Data/ Results:
Synthesis of cyclododecanone:
Cyclododecanol| 0.2691 (g)|
Sodium hypochloride| 2.300 (ml); positive for 1 time test (purple/black)| Watch glass | 49.1541 (g)|
Watch glass + cyclododecanone| 49.2172 (g)|

Crystallization of cyclododecanone:
Compound| Theoretical yield | Experimental yield| Percent yield | Melting point| Cyclododecanone| 0.2662 (g)| 0.0633 (g)| 23.78 (%)| 57.5 – 59.3 (0C)|

* Theoretical yield:
0.2691 g cyclododecanol×1 mol cyclododecanol184.32 g cyclododecanol×1 mol cyclododecanone1 mol cyclododecanol182.31 g cyclododecanone1 mol cyclododecanone
=0.2662 g cyclododecanone
* Percent yield:
Mass of actual yieldMass of theoretical yield×100%=0.0633 g cyclododecanone0.2662 g cyclododecanone×100%=23.78 % Theory/ Introduction:
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...
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