Creating A Ketone Through An Oxidation Reaction Using A...

The objective of this lab was to create a ketone through an oxidation reaction using a using a secondary alcohol and oxidizing agent in order to use that ketone in a reduction reaction with a specific reducing agent to determine the affect of that reducing agent on the diastereoselectivity of the product. In the first part of this experiment, 4-tert-butylcyclohexanol was reacted with NaOCl, an oxidizing agent, and acetic acid to form 4-tert-butylcyclohexanone. In the second part of this experiment, 4-tert-butylcyclohexanone was reacted with a reducing agent, either NaBH4 in EtOH or Al(OiPr)3 in iPrOH, to form the product 4-tert-butylcyclohexanol. 1H NMR spectroscopy was used to determine the cis:trans ratio of the OH relative to the tert-butyl group in the product formed from the reduction reaction with each reducing agent. Thin-layer chromatography was used in both the oxidation and reduction steps to ensure that each reaction ran to completion. In an oxidation reaction, the number of C-H bonds decreases or the number of C-O bonds increases, while in a reduction reaction, the number of C-H bonds increases or the number of C-O bonds decreases. In the oxidation step of this reaction, 4-tert-butylcyclohexanone is formed from when a C-H bond is lost while a C-O bond is gained to create a carbonyl. In the reduction step, 4-tert-butylcyclohexanol is formed when the carbonyl is converted into an alcohol when a nucleophilic hydride attacks the carbonyl. Whether the OH is in theShow MoreRelatedChemistry Experiment : Oxidation Of Borneol1607 Words   |  7 Pages Experiment 3: Oxidation of Borneol to Camphor By: Evan Holley Lab partner: Jeffrey Horton T.A.: Garret CHM2211L-008 07/12/2015 Introduction The overall goal in this lab was to oxidize borneol, a secondary alcohol, into camphor, which is a ketone. For the purposes of oxidation chromic acid was utilized, which was prepared by adding a 1:1 ratio of chromium trioxide to dilute sulfuric acid. The oxidation reaction occurs as a two-step reaction. The first step involves the formationRead MoreMultistep Synthesis of Benzilic Acid2109 Words   |  9 PagesMulti-Step Synthesis of Benzilic Acid from Benzoin Abstract: The main purpose of this experiment was to convert a secondary alcohol to a ketone, utilizing a mild and selective oxidizing agent. In addition, this converted alpha diketone was then subjected to rearrangement to a carboxylate salt, then acidification, to produce an alpha-hydroxyacid. In this experiment, benzoin was used and converted into benzil, which was then used to synthesize benzillic acid. The yields were not ideal: .081g of benzil-Read MoreAdipic Acid43555 Words   |  175 Pagesproductions of adipic acid in the world. 2. General Description Generally, adipic acid has a structure of  Carbon 6 straight-chain with two carboxylic acid (-COOH) groups. Due to its long aliphatic chain, it is slightly soluble in water, alcohol and acetone. Adipic acid can also be called as 1,4-butanedicarboxylic acid, 1,6-hexanedioic acid, adipinic acid, acifloctin, acinetten, octafluorohexanedioic acid as well as hexanedioic acid. It is expected to have a chemical formula of C6H10O4 and