This experiment set out to synthesize 2-methyl-4-heptanone from the supplied starting materials containing four carbons. During week one, 1-chloro-2-methylpropane was reacted with magnesium to form the Grignard reagent. The Grignard was then reacted with butanal to produce 2-methyl-4-heptanol. Using IR spectroscopy, the success or failure of the formation of the alcohol was observed, concluding week one. During week two, 2-methyl-4-heptanol was oxidized in order to form our desired product of 2-methyl-4-heptanone. Both a GC and IR spectroscopy were observed in order to determine the presence of a newly formed ketone. The results of our experiment from the IR taken during week one showed no formation of an alcohol. The GC and IR spectroscopy …show more content…
Instead, the GC and IR spectroscopy showed the presence of an aldehyde, as opposed to the desired product of a ketone. The failure of this experiment was likely caused by a null reaction between 1-chloro-2-methylpropane and magnessium, leading to no, or very little, Grignard reagent being formed. The mixture between the 1-chloro-2-methylpropane and magnessium was conducted over an extended time period with exessive amounts of reagent used in order to attempt to push the reaction forward. However, it is believed that these extreme tactics lead to a false-positive in the formation of the Grignard reagent and produced negative repercussions down the line when further experimentation was conducted. The data obtained by the IR spectroscopy from the conclusion of week one supports this theory. The presence of a carbonyl group, with an intensity of 72.40%, and no measurable formation of alcohol were observed. The oxidation of 2-methyl-4-heptanol can neither be deemed a success, nor a failure, due to it not existing in any measurable rate within our final product from week one. However, the mixture still underwent the oxidation process in an attempt to produce any possibility of the desired product. Using IR spectroscopy, the resulting data from the oxidation appeared very similar to that of the IR spectroscopy data from week one, with a slightly lower intensity of the carbonyl group at 66.89%. The GC performed on the final product mixture revealed this carbonyl group to be an aldehyde, as previously
In the Cannizaro reaction an aldehyde is simultaneously reduced into its primary alcohol form and also oxidized into it 's carboxylic acid form. The purpose of this experiment is to isolate, purify and identify compounds 1 and 2 which contain 4-chlorobenzaldehyde, methanol, and aqueous potassium hydroxide. Compounds 1 and 2 are purified by crystallization. . The purified product will be characterized by IR spectroscopy and melting point.
After 10 minutes the reaction liquid was separated from the solid using a vacuum filtration system and toluene. The product was stored and dried until week 2 of the experiment. The product was weighed to be 0.31 g. Percent yield was calculated to be 38.75%. IR spectra data was conducted for the two starting materials and of the product. Melting point determination was performed on the product and proton NMR spectrum was given. The IR spectrum revealed peaks at 1720 cm-1, which indicated the presence of a lactone group, and 1730 cm-1, representing a functional group of a carboxylic acid (C=O), and 3300cm-1, indicating the presence of an alcohol group (O-H). All three peaks correspond with the desired product. A second TLC using the same mobile and stationary phase as the first was performed and revealed Rf Values of 0.17 and 0.43for the product. The first value was unique to the product indicating that the Diels-Alder reaction was successful. The other Rf value of 0.43 matched that of maleic anhydride indicating some
Abstract: Using hypochlorous acid to convert secondary alcohol called cyclododecanol to the corresponding ketone which is cyclododecanone by oxidation.
In this experiment, the reduction of a ketone to an alcohol using sodium borohydride was demonstrated. When the solution turned from yellow to colorless, sulfuric acid was added and the solution was set under reflux to allow for the complete dissolution of the solids. After cooling, the product was then isolated using vacuum filtration before mixed solvent recrystallization was used on it. An infrared (IR) spectra was obtained for the product along with the melting point and weight. The weight was further used to calculate the percent yield.
3. The IR spectrum of the starting material shows a medium/strong C-O bond at around 1500cm-1, also the starting material shows a strong C-H bond at around 3000cm-1 and another medium C-H bond at 2865cm-1 indicating an aldehyde group whereas the product does not. The IR spectrum of the product shows a two weak broad O-H peaks at around
During the halogenation reactions of 1-butanol, 2-butanol, and 2-methyl-2-propanol, there is a formation of water from the OH atom of the alcohol, and the H atom from the HCl solution. The OH bond of the alcohol is then substituted with the Cl atom. Therefore all of the degrees of alcohol undergo halogenation reactions, and form alkyl halides as products. This is because the functional group of alkyl halides is a carbon-halogen bond. A common halogen is chlorine, as used in this experiment.
The purpose of this experiment was to synthesize the Grignard reagent, phenyl magnesium bromide, and then use the manufactured Grignard reagent to synthesize the alcohol, triphenylmethanol, by reacting with benzophenone and protonation by H3O+. The triphenylmethanol was purified by recrystallization. The melting point, Infrared Spectroscopy, 13C NMR, and 1H NMR were used to characterize and confirm the recrystallized substance was triphenylmethanol.
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 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 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
Grignard reagents are form when an alkyl halide is treated with magnesium to have the form of R-Mg-X. Grignard reagents are typically very strong nucleophiles because of the difference between the carbon and magnesium’s electronegativity. Alcohol typically is a result of a Grignard reaction. The reaction involves reacting a Grignard reagent with a carbonyl. The purpose of this experiment is to prepare a triphenylmethanol. The success of the experiment can be proved by comparing the boiling point that is provided and by using the reading of an IR spectrum.
The products of interest within this experiment are 2-methyl-1-butene and 2-methyl-2-butene from sulfuric acid and phosphoric acid catalyzed dehydration of 2-methyl-2-butanol. The reaction mixture was then separated into its separate alkene components by steam distillation and then analyzed by gas chromatography (GC), Infrared Radiation (IR) spectroscopy, and Nuclear Magnetic Resonance (NMR) imaging. Gas chromatography is an analytical technique that is able to characterize if specific compounds exist in a reaction mixture, even if they are in low quantities, assess how much of a compound exists within a reaction mixture relative to other components within the sample, and determine the purity of an isolated product. In the case of this experiment, gas chromatography is used to analyze how pure the alkene reaction sample was and if any remnants of impurities or 2-methyl-2-butanol remained in the sample after isolation of alkene components.
Objective: The purpose of this experiment was to synthesize adipic acid from cyclohexanol via an oxidation reaction that was catalyzed by sulfuric acid. Purity of the product was assessed by measuring the melting point.
The main purpose of this experiment was to synthesize benzilic acid from benzoin. This requires a multistep synthesis with benzyl as an intermediate product. The first step required HNO3 as an oxidizing agent and the second step required KOH and HCl. The percentage yields of benzil and benzilic acid were 59.5% and 21.9% respectively. The calculated melting point of benzil was 90.1-91.6 which suggested some impurities, but the MP of benzilic acid was 149.3-151.5 which suggested a pure yield. The IR further confirmed the identity of benzylic acid with two
The characteristic infrared spectra of dried-water based extract and the other three solvent extracts; hydroalcoholic (70 % ethanol), ethanol and hexane, are given in figure 2. The hexane extract shows a remarkable structural differences relative to the other three extracts with reduced absorption intensity in the hydroxyl peak (4000-3000 cm-1), increased absorption intensity in the stretching vibration of methyl and methylene CH (3000 - 2800 cm-1) and in the absorption peak that detected around 1710 cm-1 (Carbonyl bond ). These absorption characteristics