The Diel-Alder Nucleophilic Acyl Substitution

Theory: One of the methods of preparing alkyl halides is via the nucleophilic substitution reactions of alcohols. Alcohols are inexpensive materials and easy to maintain. However, they are a poor leaving group the OH group is a problem in nucleophilic substitution, this problem is fixed by converting the alcohol into H2O.

The current experiment sought to prepare 1,6-hexanedioic acid (adipic acid) by catalytic oxidation of cyclohexene in the presence of a phase-transfer catalyst (Aliquat 336), using sodium tungstate as a catalyst and hydrogen peroxide as an oxidant.

Introduction – A double replacement reaction is a chemical reaction between two compounds where the positive ion of one compound is exchanged with the positive ion of another compound. If you have the reactants of two reaction solution that you can determine the products. All you need to do is pair the positive parts of the compounds with the other compounds negative part. Once you find the products you can determine their phase of matter by using Table H. You can also use Table F to determine the solubility guidelines for aqueous solutions. If the product falls under soluble or exceptions to insoluble it is in the aqueous stare. If the product falls under

We used TLC analysis to identify each product obtained from the dihydroxylation reactions by spotting a TLC plate with the product of our reaction, a solution of cis-cyclohexane, trans-cyclohexane, and a 50:50 mixture of the two. We then placed the plate in a beaker with ethyl acetate saturating the atmosphere to allow the TLC plate to develop. Finally, we compared Rf values of the components of the mobile phase, after the phase was completed. 100% ethyl acetate was used instead of 100% Hexane or a mixture of Ethyl Acetate, because ethyl acetate has high polarity and can separate the components of a mixture to elution, unlike hexane, which is non-polar, and therefore unable to separate the components of the mixture. A 50:50 mixture of both would not work, because the polar and non-polar compounds would neutralize the mixture, and thereby not separate the components of the mixture.

The objective of this laboratory experiment is to study both SN1 and SN2 reactions. The first part of the lab focuses on synthesizing 1-bromobutane from 1-butanol by using an SN2 mechanism. The obtained product will then be analyzed using infrared spectroscopy and refractive index. The second part of the lab concentrates on how different factors influence the rate of SN1 reactions. The factors that will be examined are the leaving group, Br – versus Cl-; the structure of the alkyl group, 3◦ versus 2◦; and the polarity of the solvent, 40 percent 2-propanol versus 60 percent 2-propanol.

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 goals in this lab were to have a reaction occur with 4-methylcyclohexanol and an acid catalyst to form our product of 4-methylcyclohexene via an E1 reaction. This reaction is accomplished by removing the –OH group on 4-methylcyclohexanol via dehydration and to have a double bond form via a loss of a hydrogen on a β-Carbon.

1. Purpose: to clarify the mechanism for the cycloaddition reaction between benzonitrile oxide and an alkene, and to test the regiochemistry of the reaction between benzonitrile oxide and styrene.

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.

Distillation. Transfer the clear liquid to a dry 25-mL round-bottom flask using a Pasteur pipet. Add a boiling stone and distill the crude t-pentyl chloride in a dry apparatus. Collect the pure t-pentyl chloride in a receiver cooled in ice. Collect the material that boils between 78°C and 84°C. Weigh the product and calculate the percentage yield.

The purpose of this experiment is to examine the reactivities of various alkyl halides under both SN2 and SN1 reaction conditions. The alkyl halides will be examined based on the substrate types and solvent the reaction takes place in.

The purpose of this lab was to synthesize triphenylmethanol from benzophenone and bromobenzene by the formation of a Grignard compound with the reagents bromobenzene and magnesium metal. The bromobenzene was first transformed into the Grignard compound and was then reacted with the benzophenone to make the final product. The mixture was then mixed with sulfuric acid and the organic layer was extracted via a separatory funnel. The mixture was then recrystallized from methanol and was allowed to dry and the percent yield, melting point, and the IR was obtained. The mass of the product obtained was 5.45 grams and the percentage yield was determined to be 41.95%. The melting point range obtained from the final product was 89-91°C

The purpose of this lab is to understand the process of eliminating an alkyl halide to form an alkene. The experiment is carried out by first converting the alcohol, 2-methy-2-butanol, into the alkyl halide of 2-chloro-2-methylbutane that will then be put through dehydrohalogenation that favors elimination reaction (E2) to create a mixture of 2-methyl-2-butene and 2-methyl-1-butene. A fractional distillation will be taken to purify the mixture and an additional gas chromatography will be done to further analyze the mixture composition. A bromide test will be done to determine the product of an alkene in the experiment.

This lab consisted of the conversion of alcohols into alkyl halides through common substitution methods. These methods include SN1 and SN2 mechanism, both of which can occur for this type of reaction. For both reactions, the first step of protonation will be to add hydrogen to the –OH group and then the rest of the reaction will proceed according to the type of mechanism. SN1 reactions form a cation intermediate once the H2O group leaves, then allowing a halide (such as Br) to attack the positively charged reagent1. On the other hand, SN2 reactions are one-step mechanism in which no intermediate is formed and the halide attaches as the leaving

Arylamine N-acetyltransferases (NATs) (EC 2.3.1.5) are a family of phase II drug metabolizing enzymes that acetylate primary hydrazine and arylamine xenobiotics in prokaryotes and eukaryotes. In humans, there are two closely related isoenzymes, NAT1 and NAT2. Both of their genes are located at chromosome 8p22 with 87% nucleotide sequence identity (1). NAT2 is primarily limited to the liver and gastrointestinal tract but still attracted most interest because of its ability to acetylate various drugs. By contrast, NAT1 is widely distributed in tissues with a greater affinity for small arylamines. The finding of NAT1 expression during embryonic development and pregnancy indicates that NAT1 might play an important role in cell biology besides