Oxidation of cyclohexanone to adipic acid essay

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The cyclic ketone cyclohexanone was oxidized to adipic acid using the oxidizing agent nitric acidity. The test yielded zero. 2667 grams of adipic acid, providing an percent produce of 113. 97%. Although the product was allowed to dry for one week, residual moisture was still within the test and a melting level could not become obtained. This kind of error inside the experiment both resulted from adding a lot of water or not allowing for the product to remain in the Hirsch vacuum purification for long enough to sufficiently dry.


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Redox reactions invariably is an important course of reactions in organic and natural chemistry that involve the transfer of electrons from molecule to another. This try things out focused on a great oxidation response. In organic and natural chemistry, oxidation process reactions arise when a co2 atom turns into bonded to a much more electronegative atom, causing the electron denseness on the carbon dioxide atom to decrease (McMurray, 2012). Examples of oxidation reactions in organic biochemistry are the disregarding of a carbon-hydrogen bond, or perhaps the formation of any carbon-oxygen connect (McMurray, 2012).

This kind of reaction oxidized a secondary alcoholic beverages to a ketone (Williamson, 2003). The oxidation process of a ketone, in this case, cyclohexanone, can be achieved by using numerous oxidizing brokers, however , this kind of experiment used the powerful oxidizing agent nitric acidity. An advanced is formed within this oxidation, which is further oxidized to adipic acid (Figure 1) (Williamson, 2003). This reaction features particular importance, as it fails the cyclic carbon diamond ring when adipic acid is created (Williamson, 2003).

The ketone reagent used in this experiment was cyclohexanone, a cyclic six-carbon ring with a great attached oxygen group (Figure 1). Cyclohexanone is a great oily crystal clear liquid for room temperatures. Cyclohexanone is known to have the molecular formula, C6H10O, a molecular weight of 98. 13 grams/mole, a melting level of -47 C and a thickness of zero. 9 grams/mL. (PubChem. com) The oxidizing agent utilized in this experiment was 15 M nitric acid (Figure 1), a colorless or yellowish, fuming, corrosive the liquid at room temperature. Nitric acid gets the chemical formulation HNO3, a molecular fat of 63. 01 grams/mol, a shedding point of -42 C, and a density of 1. 5027 grams/mL. (PubChem. com)

The product produced in this response was adipic acid (Figure 1), a white transparent solid material at room temperature, which can be deprotonated two times. Adipic acidity is an important professional chemical employed in the activity of nylon. Adipic chemical p has the molecular formula, C6H10O4, the molecular weight 146. 14 grams/mol, a shedding point of 153 C, and a density of 1. 36 g/cm3. (PubChem. com) Figure 1 . Reaction system for the reduction of cyclohexanone to adipic acidity, using the oxidizing agent nitric acid. Determine 1 . Reaction mechanism intended for the lowering of cyclohexanone to adipic acid, using the oxidizing agent nitric acid solution.


This kind of experiment was conducted beneath conditions referred to by Williamson, 2003. To begin, approximately a hundred and fifty mg of cyclohexanone was placed into a vial. In a separate 15 x 75 mL reaction tube, 1 ) 0 mL of HNO3 was added by pipette, along with a pre-weighed boiling nick. The reaction tube containing the nitric acid was clamped into a fine sand bath beneath the fume cover and heated at a minimal setting. One particular drop of cyclohexanone was careful included in the nitric acid. The existence of a brown oxide mentioned that the response had started, at which point the reaction tube was removed from the sand bathtub. Cyclohexanone was added to the reaction tube drop wise.

Added cyclohexanone was not added to the response tube before the previous response had finished. After the previous drop of cyclohexanone was added, the response tube was placed back in the fine sand bath and boiled for starters minute. The tube was then taken from the crushed stone bath and allowed to cool to room temperature prior to being put into an ice bath for 3 minute. Three drops of water had been added to the reaction tube while it remained in the ice bathtub. The product was collected by Hirsch vacuum pressure filtration and allowed to dried out for the time of one week before weight and burning point were obtained.


The test yielded zero. 2667 grams of adipic acid, providing an percent yield of 113. 97% produce. The product included residual wetness and has not been in a solid state, to ensure that a shedding point cannot be obtained.


The adipic chemical p produced by this experiment even now contained wetness and had not been in a stable state following one week, giving a large amount of inaccuracy in the percent deliver and not allowing for a burning point to be taking. This is relatively limiting, in this a discuss the chastity of the merchandise cannot be presented without a burning point. The merchandise was likely too wet because it has not been allowed to dry long enough inside the Hirsch vacuum filtration method. Adipic acid is also extremely soluble in water, to ensure that adding too much water even though the product was one ice bath might have mixed some of the uric acid (Gaivoronskii & Granzhan, 2005). The degree to which the adipic acid is definitely soluble in water has also been found to depend on the temperature (Gaivoronskii & Granzhan, 2005). In future experiments, experts recommend to allow the item to dry much longer in the vacuum pressure filtration process and to physical exercise more care when adding water for the crystals to assure product is certainly not lost.


Gaivoronskii AN, Granzhan, VETERANS ADMINISTRATION (2005). Solubility of Adipic Acid in Organic Solvents and Normal water. Russian Journal of Utilized Chemistry. 79 pp 404-408. McMurray, JM (2012). Organic Chemistry, 9th Edition. CENGAGE Learning. Williamson, KL (2003). Macroscale and Microscale Organic and natural Experiments, next Edition. Houghton Mifflin Customized Publishing. PubChem. com (2012). National Center for BioTechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=944&loc=ec_rcs Accessed Feb . 20, 2013.

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