Alkyl Aryl Ether Synthesis Essay

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.

Grignard reagents are reactive enough to also attach esters; however, two equivalents of the Grignard reagent are usually added because less then two equivalents leave a large quantity of unreactive ester. This reaction forms a tertiary alcohol.

The two remaining sp2 hybrid orbitals on oxygen are used to hold oxygen's lone pairs(bruice). O-ethylsaccharin is then less stable because the Ethyl group is attached to the Oxygen that used to be a carbonyl group, giving the Carbon an sp3 configuration (joined to two other carbons, the Oxygen with the Ethyl group and a Hydrogen). This put strain on the ring, and therefore is less stable.”(Richard y.a.). Upon mixing the reactants, sodium saccharin slightly dissolved producing a clear colorless liquid. When placed at 80°C hot bath, the solution completely dissolved and turned yellowish-green. Iodoethane is a clear and colorless liquid, but when exposed to light and air the Iodide dissociates from ethane and gives off a yellow color as a sign of decomposition. The solution was covered to prevent this from happening. But, as iodide dissociates from CH3CH2 that then gave off its yellowish color which shows SN2 reaction taking place. SN2 reaction happened fast The limiting Reagent is Iodoethane , as the alkylating agent; it was not used in excess and dictated how far the reaction went. The Na+ binds with I-(noted disappearance of the yellow color, as I- binds with Na+) then the ethane group bonds with either the Oxygen of saccharin or the Nitrogen of saccharin. The final product after vacuum filtration had some unreacted material, indicated by some yellow green solid formation.

The first TLC plate showed that the fractions collected during the experiment that appeared to be the purest were fractions 4 and 6. These two fractions and fractions number 5 were combined for the final product. The Rf values for the standard carvone, fraction 4, and fraction 6 were all 0.32 indicating that these compounds were

The solution that was performed in this experiment was to use sulfuric acid in order to form a protonated alcohol, so when the halogen or nucleophile back attacks the compound, water is displaced. Once the alcohol is protonated, the solution reacts in either an SN1 or SN2 mechanism.

The reaction created in the lab was a condensation reaction, specifically a fischer esterification reaction. This reaction is created by combination of a carboxylic acid and alcohol group with loss of water. A very noticible property of ester products are the oders they produce, which is usually described as fruity. For example, propyl methanoate is described as smelling like apples. Butyl heptanoate has a distinct sent of coconut. Also pentyl ethanoate has a banana scent when created. Lastly propyl butanoate is described as smelling like pears.

First, dichloromethane was the least polar solvent, so it barely moved up the plate. Hence, the spots on the TLC plate stayed at almost the same place they were spotted on, and separation did not occur. As a result, the retention factor (Rf) values for these components were too small. In addition, the second solvent, methanol, was the most polar solvent out of the three, and the solvent moved up the plate too quickly. This resulted in the components moving up the plate based on the solvent's polarity instead of their own, and a smear of all components at the solvent front was observed. Hence, the Rf values could not be determined. Lastly, ethyl acetate, a moderately polar solvent, moved up the plate with moderate speed. This gave the components time to move up the plate according to their polarity, and the Rf values could be used to identify the unknown compound. According to the TLC method with ethyl acetate solvent, the unknown compound had the same Rf value with acetanilide (Rf = 0.40). As a result, the unknown compound was identified as

One supporting evidence is that the resulting infrared spectra in Figure 2 for the product still contains an OH stretch of 3343 cm-1. In fact, the stretch of OH in the product is broader than the stretch of the starting material in Figure 1. This could imply that the layers in the separatory funnel initially did not form, although a lot of time has taken to settle. Adding 10% sodium chloride to the mixture helped to form layers, but that does not necessarily mean that the –OH group had completely separated from the carbocation. And so, the resulting product is not pure. Furthermore, it is expected that the C-Cl stretch (between 850 to 550 cm-1) and C-H wag (1300-1150 cm-1) should appear on Figure 2, but that did not happen. Moreover, the reaction failed since the amount of tert-amyl alcohol used was not a lot enough to form an expected

The NMR spectra solution #33 (the unknown) matched closest to that of 4-tert-butylbenzylphenolether 14) The yield (.468 g) makes sense because it was lower than the theoretical yield calculated (1.57 g). Yield may have been lost because the crystals formed too quickly, causing some of them to be small in size and seep through the filter and into the filtrate. 15) The percent recovery of 55.7% makes sense.

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

After drying out the product and recrystallizing it for weighing, it was determined that the total weight of the product was 0.091g which gave a percent yield of 32.535%, meaning that the overall the reaction was successful however there are quite a few areas for improvement in this experiment to increase the yield of the reaction. The melting point of the product was taken to be 170.7 degrees C meaning that the product produced, despite having a low yield, was in fact acetaminophen and not p-aminophenol which would have melted at a higher temperature of 188-190 degrees C. Looking at the TLC plate it was shown that the reaction did in fact reach completion because the final reaction mixture eluted as far as the acetaminophen standard and not as far as the p-aminophenol standard, meaning that the acetaminophen standard and the reaction mixture had the same contents, without and p-aminophenol. Finally looking at the IR spectrum, there is a peak at around 3320 cm-1 which signifies a N-H amide stretch, there is a broad peak at about 3107 cm-1 which is the phenolic OH stretch, and is broadened by the strong hydrogen bonding.

Discussion: The focus of the first part of the experiment is extraction. By using liquid-liquid extraction, the acid, base and neutral component of an unknown compound should be isolatable. The unknown compound was in a 1:1:1 ratio of acid, base and neutral components. By dissolving it in 20mL of ethyl acetate, then adding it to a separatory funnel with 20mL of HCl, the HCl would be expected to react with the unknown base in the separatory funnel.

where R was the gas consistent (8.314 J K-1 mol-1), T is the absolute temperature (K) and 55.5 was the water concentration. The high values of Kads and negative values of ∆G_ads^° proposed that, RSWP molecules emphatically adsorbed on the metal surface. For the most part, values of ∆G_ads^° up to –20 kJ mol-1 are physically adsorbed with the electrostatic communication between the charged particles and the charged metal, while those more negative than –40 kJ mol–1 are chemically adsorbed include sharing or exchange of electrons from the inhibitor atoms to the carbon steel surface to form a coordinate bond [35]. In the present investigation, the acquired estimation of ∆G_ads^° for RSWP was found –50 kJ mol–1. This, demonstrate that the adsorption

Abstract: A mechanism of the initiated nonbranched-chain process of forming 1,2-alkanediols and carbonyl compounds in alcohol–formaldehyde systems

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