Experiment 3: Oxidation of Borneol to Camphor
By: Evan Holley
Lab partner: Jeffrey Horton
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 formation of chromate esters and the second step is an elimination reaction that will produce the carbonyl group necessary to make either a ketone or an aldehydes. The reaction is hallmarked by the breaking of a C-H bond and the formation of a C-O bond (James, 2014). Specifically when oxidizing alcohols, it is important to note that primary alcohols can be converted to aldehydes as well as completely to carboxylic acids, secondary alcohols are converted to ketones and no further, and tertiary alcohols cannot be oxidized. The oxidizing agent removes the hydrogen from the –OH group and the hydrogen from the C-H group attached to the –OH group in a compound. Tertiary alcohols cannot be oxidized because they lack the C-H bond that is present in both the oxidation of primary and secondary alcohols (Clark, 2003).
The conditions for this type of reaction vary depending on what degree of alcohol you are trying to oxidize. In our case, we oxidized a secondary alcohol at room temperature. It was
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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 the
The Hydroxyl group on alcohols relates to their reactivity. This concept was explored by answering the question “Does each alcohol undergo halogenation and controlled oxidation?” . Using three isomers of butanol; the primary 1-butanol, the secondary 2-butanol and the tertiary 2-methyl-2-propanol, also referred to as T-butanol, two experiments were performed to test the capabilities of the alcohols. When mixed with hydrochloric acid in a glass test tube, the primary alcohol and secondary alcohols were expected to halogenate, however the secondary and tertiary ended up doing so. This may have been because of the orientation of the Hydroxyl group when butanol is in a different
The Purpose of this experiment is for the students to learn how to use sodium borohydride to reduce benzil to its secondary alcohol product via reduction reaction. This two-step reaction reduces aldehydes by hydrides to primary alcohols, and ketones to secondary alcohols. In order for the reaction to occur and to better control the stereochemistry and yield of the product, the metal hydride nucleophile of the reducing agents such as LiH, LiAlH4, or NaBH4 must be carefully chosen. Being that LiAlH4 and NaBH4 will not react with isolated carbon-carbon double bonds nor the double bonds from aromatic rings; the chosen compound can be reduce selectively when the nucleophile only react with
If another enzyme like lactase is used, no reaction would take place because the substrate, hydrogen peroxide, wouldn’t fit into the active site.
Introduction: Reaction of a compound with water can result in a splitting, or lysis, of the compound into two parts. Organic molecules containing a group of atoms called an ester can be hydrolyzed by water to form a –COOH group (carboxylic acid) and an HO-- group (alcohol) as follows:
Catechol oxidase is an enzyme that speeds up the oxidation reaction when catechol is exposed to oxygen. When the reaction occurs, benzoquinone is produced turning the oxidized substance brown. It was hypothesized that the higher the concentration of catechol oxidase, the browner the substance will turn, and the faster it will achieve the color. In the present lab, different concentrations of catechol oxidase were mixed with pure catechol and the rate at which each solution browned was measured using a colorimeter. The
Abstract: Using hypochlorous acid to convert secondary alcohol called cyclododecanol to the corresponding ketone which is cyclododecanone by oxidation.
This experiment was designed by conducting a substitution reaction to construct a complex compound (2-methylphenoxyacetic acid) from two simple parts; also known as synthesis - converting simple molecules into more complex molecules. A purification technique known as crystallization was used to purify the product. Suction filtration was used to filter out the product. The experiment was completed over a three-day experimental period.
The Grignard reaction is an important synthetic process by which a new carbon to carbon bond is formed. Magnesium metal is first reacted with an organic halide forming the Grignard reagent. The Grignard reaction is the addition of an organomagnesium halide (Grignard reagent) to a ketone or aldehyde, to form a tertiary or secondary alcohol, respectively. For example, the reaction with formaldehyde leads to a primary alcohol. Grignard Reagents are also used in the following important reactions: The addition of an excess of a Grignard reagent to an ester or lactone gives a tertiary alcohol in which two alkyl groups are the same, and the addition of a
In this experiment, the main objective was to synthesize a ketone from borneol via an oxidation reaction and secondly, to produce a secondary alcohol from camphor via a reduction reaction. Therefore, the hypothesis of this lab is that camphor will be produced in the oxidation reaction and isoborneol will be the product of the reduction reaction because of steric hindrance. For the oxidation step, a reflux will be done and then a microscale reflux for the reduction step. The products will be confirmed using Infrared spectroscopy, the chromic acid test, 2,4-DNP test and 13C NMR spectroscopy. The results of this
The reaction took place in a conical vial and .2mL of each of the reactant samples were added to it along with some 95% ethanol. Two drops of NaOH were added shortly after and stirred at room temperature for fifteen minutes. The vial was cooled in and ice bath and crystallized. Vacuum filtration was performed to filter the crude product. The crude product was recrystallized using methanol and filtered again. We made one change to the procedure and instead of using .7mL of ethanol we
The method used in this experiment is called an oxidation reaction. An oxidizing agent takes away electrons from other reactants during a redox reaction. The oxidizing agent typically takes these electrons for itself, thus gaining electrons and being reduced (Helmstein, Ph. D 2017). The organic oxidant used in this experiment is sodium hypochlorite, which is also known as “household bleach’. Sodium hypochlorite in acetic acid is an alternate oxidizing agent used for the development of ketones that was developed by Stevens, Chapman and Weller due to the many advantages it displays (J. Org. Chem, 1980, 45, 2030). This particular oxidation of sodium hypochlorite is an exothermic reaction meaning that it releases heat as an energy form. Due to the exothermic nature of this experiment, temperature ranges should be monitored throughout the experiment. The overall objective in this experiment is to yield a