Bromination Lab Report

The purpose of this lab is to examine the composition of three components of gas products of elimination reaction under acidic condition by conducting the dehydration of primary and secondary alcohol, and under basic condition by conducting the base-induced dehydrobromination of 1-bromobutane and 2-bromobutane. Then gas chromatography is used to analyze the composition of the product mixtures.

Abstract – Methyl trans-cinnamate is an ester that contributes to the aroma of strawberry. It can be synthesized by an acid-catalyzed Fischer esterification of a methanol and trans-cinnamic acid under reflux. The solution was extracted to obtain the organic product, and evaporated residual solvent The yield was 68%, but there is some conflicting data regarding the purity. The melting point, IR, GC-MS indicate a highly pure desired product whereas 1H NMR shows there are unreacted reagents still present.

The purpose of this experiment was to be able to synthesize triphenylmethyl bromide from triphenylmethanol by a trityl carbocation intermediate. During the experiment, 0.100 g of triphenylmethanol was placed into a small test tube. The triphenylmethanol looked like a white powder. Next 2 mL of acetic acid was added to the test tube and the solution turned a cloudy white color. There was a strong odor similar to the smell of vinegar given off. After the solution was heated and the solid dissolved, 0.2 mL of hydrobromic acid was added to the test tube. The solution turned a bright yellow color after the hydrobromic acid was added. The solution was heated in a hot water bath for 5-10 minutes and then let cool. After heating, the

Experiment 3 comprised three reactions: formation of dimethyl tetraphenylphthalate, hexaphenylbenzene, and tetraphenylnaphthalene. All 3 reactions used tetraphenylcyclopentadienone as the diene to generate products with high aromatic stabilization.

This procedure was undertaken in order to convert a primary alcohol, 1-butanol, into a primary alkyl halide, 1-bromobutane. This was done using hydrobromic acid. Additionally, tests were performed to assess the degree of the alkyl halide: primary, secondary or tertiary. These tests were the silver nitrate test and the sodium iodide test. The goal of these tests was to verify that 1-bromobutane, a primary alkyl halide, had in fact been formed.

The purpose of this experiment was to learn about metal hydride reduction reactions. Therefore, the sodium borohydride reduction of the ketone, 9-fluorenone was performed to yield the secondary alcohol, 9-fluorenol. Reduction of an organic molecule usually corresponds to decreasing its oxygen content or increasing its hydrogen content. In order to achieve such a chemical change, sodium borohydride (NaBH4) is used as a reducing agent. There are other metal hydrides used in the reduction of carbonyl groups such as lithium aluminum hydride (LiAlH4). Nevertheless, the latter is not used in this experiment since it is very reactive and extremely flammable. On the contrary, NaBH4 is relatively mild and it can be used with protic solvents.

1,2,3,4-tetraphenylnaphthalene is prepared by first producing benzyne via the unstable diazonium salt. Then tetraphenylcyclopentadienone and benzyne undergo a diels-alder reaction to create 1,2,3,4-tetraphenylnaphthalene.

As seen in table 1, the theoretical yield was .712 g of C_17 H_19 NO_3. The % yield of this experiment was 7.51 % of C_17 H_19 NO_3. . This low yield can be explained from a poor recrystallization technique combined with potential contamination. Throughout the experiment, the mixture changed color from green, orange, to yellowish lime, and eventually clear. These color changes indicate a chemical change, which show that a reaction had occurred. In the first step when o-vanillin and p-toludine, imine was formed. The color change from green to orange suggests that imine appears as orange colored. In the second step, the addition of sodium borohydride reduced the imine into another derivative, which was yellowish lime color. The solution turned clear when acids and anhydrides was added, which indicated the precipitate were dissolved. However, after refluxing for a while, yellow precipitates begin to form near the top of the flask. It was assumed that the remaining starting material was concentrated from a decrease volume to reappeared in solution. Nevertheless, this may have been a sign of contamination that will negatively affect the entire reaction. This observation later resulted in a yellowish

In nucleophilic substitution reactions, there are two possibilities, either Sn1 or Sn2. In this particular experiment, an Sn2 reaction

Yes, the melting point data does make sense. While the melting point range was close to the given temperature range, the data was still a little lower than expected. This may have been caused by impurities in the product, since impurities cause melting point range to decrease. The product was observed moving up the capillary tube during melting point analysis, which indicates that the product was not completely dry before melting point range was taken. The water in the product evaporated and caused the product to be pushed up. It can be hypothesized that the water in the product affected the melting point

The goal of the experiment is to synthesize a bromohexane compound from 1-hexene and HBr(aq) under reflux conditions and use the silver nitrate and sodium iodide tests to determine if the product is a primary or secondary hydrocarbon. The heterogeneous reaction mixture contains 1-hexene, 48% HBr(aq), and tetrabutylammonium bromide and was heated to under reflux conditions. Heating under reflux means that the reaction mixture is heated at its boiling point so that the reaction can proceed at a faster rate. The attached reflux condenser allows volatile substances to return to the reaction flask so that no material is lost. Since alkenes are immiscible with concentrated HBr, tetrabutylammonium bromide is used as a phase-transfer catalyst. It forms a complex with HBr and extracts it from the aqueous phase into the organic phase where the alkene is. This dehydrates the acid, making it more reactive so that the addition reaction is possible. Rapid stirring is required in order to maximize the surface area

The Wittig reaction is valuable reaction. It has unique properties that allows for a carbon=carbon double bond to form from where a C=O double bond used to be located. Creating additional C=C double bonds is valuable due to its use in synthesis. The Wittig reaction will allow the synthesis of Stilbene (E and Z) from a Benzaldehyde (Ketcha, 141).

The mechanism for the synthesis of 3-nitrochalcone is presented in Figures 1 and 2. The alpha carbon on the acetophenone is deprotonated. This is followed by the attack of the alpha carbon anion on the carbonyl carbon on the 3-nitrobenzaldehyde. Next, the oxygen is protonated from the 3-nitrobenzaldehyde, which is then followed by an elimination reaction where this acts as a leaving group. The product is the trans-alkene present in the product. After the reaction was completed, purification of the product was conducted using semi-microscale recrystallization.

There are several factors which affect the rate of reaction: catalyst, reactant concentration, and temperature.1,2

The purpose of this experiment was to purify acetanilide that was contaminated with relatively small amounts of impurities using recrystallization. The success of recrystallization was dependent on a suitable solvent being chosen and proper recrystallization technique being carried out. The solvent chosen had to have a different polarity than that of the molecule of interest. The technique used was dependent on the solubility of the solvent at higher temperature and the solubility of the impurities at all temperatures. To analyze the acetanilide product of the reaction, 1H NMR and IR were used.