Glycerol: Fourier Transform Infrared Spectrometry

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.

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

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

The goal of this project was to make, and test four soaps, and two detergents. The purpose of making four different soaps and two detergents was needed in order to decide which one would be best for the environmental group to use in the future that would allow for the safest cleanup of an oil spill while not harming the animals or the environment in the process. It was necessary to test the impact of the four soaps and two detergents by analyzing their different properties based off of their specific characteristics and the wastewater left over from the vacuum filtration procedure. This procedure had to be undertaken in order to confirm which of the soaps and detergents synthesized is most

The light yellow precipitate was collected by suction filtration using a Hirsch funnel. The product was washed with two 1-mL portions of cold methanol followed by two 1-mL portions of diethyl ether. The product was dried in the oven at 110°C. The IR spectrum as a KBr pellet was obtained for the product and inosine for analysis.

liquid with a sweet, slightly acrid taste resembling that of glycerin. It is miscible with chloroform, acetone, 95% ethyl alcohol, glycerin, and water. It is soluble at 1 in 6 parts of ether and not miscible with light mineral oil or fixed oils but will dissolve in some essential oils (98).

(Ketcha, Daniel; Turnbull, Kenneth; Grieb, Jonathan. Organic Chemistry Laboratory Experiment, “Dehydration of 2-Methylcyclohexanol and Gas Chromatography.” Cincinnati, OH: Van Grinner Publishing, 2016.)

(2) Glycerol is reusable, has beneficial physiochemical properties, and can tolerate heating and mixing techniques that are not considered conventional. It can also improve product yields and enable catalysts to be recycled. All reagents are commercially available.

(Physical Constants of Organic Compounds). In addition, the obtained IR spectrum also signifies high purity of isoborneol in the sample. As demonstrated in Scheme 2 of page 2, isoborneol contains a hydroxy group in the equatorial position, which means that it is an alcohol. The predicted stretches of an alcohol are located around 3300.00 cm-1 and from 3380.00-3500.00 cm-1 in the literature spectrum, Figure 4. The IR spectrum on Figure 3 of page 7 depicts a broad stretch between 3320.00-3480.00 cm-1, signaling the presence of an alcohol functional group.

Almost everybody is familiar with the fruity scents at their local grocery store. Many of these scents are esters. Most of the aromas we know represent a mixture of esters and other molecules like alcohol. The process of making ester is known as esterification. Esters are formed carboxylic acid and a carboxylic acid reacts with alcohol, water is also produced from this reaction. Carboxylic acid contains the –COOH group (Jim Clark, 2003)

IR spectroscopy is able to determine if starting material was co-distilled due to 2-methycyclohexanl’s alcohol functional group that creates a distinct signal in the 3200 cm-1 to 3600 cm-1 range, which does not appear for the methylcyclohexene products. Also, GC is an adept method to analyze a mixture of compounds and determine the proportion of chemicals in a solution. This allows for the identification of all three products and the potential to identify impurities due to co-distillation. Both of these analytical tests are more beneficial than HNMR spectroscopy, which would not provide as much of an insight to the composition of the distillate solution and the relative amounts of each chemical that is present.

During this experiment the crude product (mixture of ortho and para nitrophenols) was run through a column chromatography. The point of the column chromatography was to separate the nitrophenols and purify them. During the experiment the crude product was ran through the silica with two different solvents. 60:40 DCM/hexanes was used to form the first band while 50:50 DCM/EtOAc was used to form the second band. The reason for this method was that there had to be a change in solvent for the para product because since it is polar it was expected to run very slowly through the column and therefore needed a more polar solvent to speed it up, ethyl acetate. As expected two different yellow bands were observed. Each band represented one of the nitrophenols, with the bottom band being the ortho-nitrophenol since it is less polar and stayed within the solvent and therefore ran through the column quickly. The para product stayed at the top because it was similarly polar to the Silica and had the ability to hydrogen bond to it. Once the bands were formed fractions were taken from the yellow bands. Fraction 1-5 was from the ortho product and fractions 6-10 were from the para product. The fractions formed were than ran through TLC chromatography to test the true purity of the products and the success of the column chromatography separation. The first TLC plate containing fractions 1-5, surprisingly did not have any spots (Figure 1b). This is was unexpected because fractions 1-5 were

The glycerol has a phosphate group which is hydrophilic –‘attracted to water’ complete opposite to the fatty acids chain which is hydrophobic – ‘scared of water’.

The aim of this experiment was to investigate different reactions between a range of alcohols and carboxylic acids to produce a variety of esters of different odours and discover how they can be used commercially in household products.

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