The cyclic ketone cyclohexanone was oxidized to adipic acid utilizing the oxidising agent azotic acid. The experiment yielded 0. 2667 gm of adipic acid. giving a percent output of 113. 97 % . Although the merchandise was allowed to dry for one hebdomad. residuary wet was still present in the sample and a thaw point could non be obtained. This mistake in the experiment either resulted from adding excessively much H2O or non leting the merchandise to stay in the Hirsch vacuity filtration for long plenty to sufficiently dry.

Introduction

Redox reactions are an of import category of reactions in organic chemical science that involve the transportation of negatrons from one molecule to another. This experiment focused on an oxidization reaction. In organic chemical science. oxidization reactions occur when a C atom becomes bonded to a more negatively charged atom. doing the negatron denseness on the C atom to diminish ( McMurray. 2012 ) . Examples of oxidization reactions in organic chemical science are the breakage of a carbon-hydrogen bond. or the formation of a carbon-oxygen bond ( McMurray. 2012 ) . This reaction oxidized a secondary intoxicant to a ketone ( Williamson. 2003 ) . The oxidization of a ketone. in this instance. cyclohexanone. can be accomplished by utilizing assorted oxidising agents. nevertheless. this experiment made usage of the powerful oxidizing agent azotic acid. An intermediate is formed during this oxidization. which is further oxidized to adipic acid ( Figure 1 ) ( Williamson. 2003 ) . This reaction is of peculiar importance. as it breaks the cyclic C ring when adipic acid is formed ( Williamson. 2003 ) .

The ketone reagent used in this experiment was cyclohexanone. a cyclic six-carbon ring with an affiliated O group ( Figure 1 ) . Cyclohexanone is an oily clear liquid at room temperature. Cyclohexanone is known to hold the molecular expression. C6H10O. a molecular weight of 98. 14 grams/mole. a runing point of -47 °C and a denseness of 0. 9 grams/mL. ( PubChem. com ) The oxidising agent used in this experiment was 15 M azotic acid ( Figure 1 ) . a colorless or yellowish. fuming. caustic liquid at room temperature. Nitric acid has the chemical expression HNO3. a molecular weight of 63. 01 grams/mol. a runing point of -42 °C. and a denseness of 1. 5027 grams/mL. ( PubChem. com )

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The merchandise yielded in this reaction was adipic acid ( Figure 1 ) . a white crystalline solid substance at room temperature. which can be deprotonated twice. Adipic acid is an of import industrial chemical used in the synthesis of nylon. Adipic acid has the molecular expression. C6H10O4. the molecular weight 146. 14 grams/mol. a runing point of 153 °C. and a denseness of 1. 36 g/cm3. ( PubChem. com ) Figure 1. Chemical reaction mechanism for the decrease of cyclohexanone to adipic acid. utilizing the oxidising agent azotic acid. Figure 1. Chemical reaction mechanism for the decrease of cyclohexanone to adipic acid. utilizing the oxidising agent azotic acid.

Experimental

This experiment was conducted under conditions described by Williamson. 2003. To get down. about 150 milligrams of cyclohexanone was placed into a vial. In a separate 10 ten 100 mL reaction tubing. 1. 0 milliliter of HNO3 was added by pipette. along with a pre-weighed boiling bit. The reaction tubing incorporating the azotic acid was clamped into a sand bath under the fume goon and heated at a low scene. One bead of cyclohexanone was careful added to the azotic acid. The presence of a brown oxide indicated that the reaction had begun. at which point the reaction tubing was removed from the sand bath. Cyclohexanone was added to the reaction tubing bead wise.

Additional cyclohexanone was non added to the reaction tubing until the old reaction had completed. After the last bead of cyclohexanone was added. the reaction tubing was placed back into the sand bath and boiled for one minute. The tubing was so removed from the sand bath and allowed to chill to room temperature before being placed in an ice bath for three minute. Three beads of H2O were added to the reaction tubing while it remained in the ice bath. The merchandise was collected by Hirsch vacuity filtration and allowed to dry for the period of one hebdomad before weight and runing point were obtained.

Consequences

The experiment yielded 0. 2667 gm of adipic acid. giving a percent output of 113. 97 % output. The merchandise contained residuary wet and was non in a solid province. so that a thaw point could non be obtained.

Discussion

The adipic acid produced by this experiment still contained wet and was non in a solid province after one hebdomad. giving a big grade of inaccuracy in the per centum output and non leting for a thaw point to be taking. This is slightly confining. in that a remark on the pureness of the merchandise can non be given without a thaw point. The merchandise was probably excessively wet because it was non allowed to dry long plenty in the Hirsch vacuity filtration procedure. Adipic acid is besides really soluble in H2O. so that adding excessively much H2O while the merchandise was one the ice bath may hold dissolved some of the crystals ( Gaivoronskii & A ; Granzhan. 2005 ) . The grade to which the adipic acid is soluble in H2O has besides been found to depend on the temperature ( Gaivoronskii & A ; Granzhan. 2005 ) . In future experiments. it is recommended to let the merchandise to dry thirster in the vacuity filtration procedure and to exert more cautiousness when adding H2O to the crystals to guarantee merchandise is non lost.

Mentions

Gaivoronskii AN. Granzhan. VA ( 2005 ) . Solubility of Adipic Acid in Organic Solvents and Water. Russian Journal of Applied Chemistry. 78 pp 404-408. McMurray. JM ( 2012 ) . Organic Chemistry. 8th Edition. CENGAGE Learning. Williamson. KL ( 2003 ) . Macroscale and Microscale Organic Experiments. 4th Edition. Houghton Mifflin Custom Publishing. PubChem. com ( 2012 ) . National Center for BioTechnology Information. hypertext transfer protocol: //pubchem. ncbi. nlm. National Institutes of Health. gov/summary/summary. cgi? cid=944 & A ; loc=ec_rcs Accessed February 20. 2013.

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