Synthesis of an Alkyne: Bromination of Stilbene and Dehydrohalogenation of Dibromide Maya Yagan Fall 2015 Lab Section 355-01 Lab Partner: Kristine Thao Abstract Trans-stilbene (1,2-diphenylethene) was synthesized in a two-step reaction. Trans-stilbene was brominated to give meso-stilbene dibromide in the first reaction. The stilbene dibromide was heated with base in order to induce dehydrobromination. One of the methods used throughout this experiment was vacuum filtration. An 81% yield was obtained due to a few minor errors. The compound seemed to be pure due to the relatively close melting point ranges. Introduction The experiment that was conducted in lab was synthesis of an alkyne. Now, what exactly is an alkyne? An …show more content…
In the first reaction, trans-stilbene was brominated to give meso-stilbene dibromide. In the second reaction, the stilbene dibromide was heated with base to induce dehydrobromination (net loss of HBr) and formation of diphenylacetylene. The purpose of this lab experiment is to carry out the bromination of E-stilbene and characterize the product, meso-stilbene dibromide, by its melting point. In the following experiment, the dibromide is converted into diphenylacetylene. Pyridinium hydrobromide perbromide (PHPB), a crystalline solid which is much less corrosive and easier to handle than liquid bromine was the brominating agent used in this …show more content…
The mixture was warmed in a hot water bath until the solid dissolved and then 1.0 g of pyridinium hydrobromide perbromide was added. With a little acetic acid, the crystals of reagent from the sides of the flask were rinsed and then heated for an additional 1-2 minutes. Immediately, stilbene dibromide precipitated as small plates. Once the mixture has been cooled under tap water, the product was collected by vacuum filtration. Ice cold methanol was used to wash and the isolated solid continued to dry for a few minutes. To achieve maximum drying, the crystals were pressed with a spatula. The yield, percent yield, and melting point of the product was recorded. About 0.8 g of stilbene bromide should’ve been obtained with an expected melting point range of 236℃-237℃. The IR spectrum was obtained and compared to that reported for the pure
The product obtained had a melting point of approximately 107 °C and a weight of .324 grams. Some of the product would not dissolve in water and so was removed through vacuum filtration, which left .141 g not dissolved in solution. It took 13.2 mL of sodium hydroxide to turn the solution of the product dissolved in water pink. A molecular weight of 138.63 g/mol was calculated from the data. These results indicate that the product was 2-methylbenzoic acid, the Grignard reagent was 2-methylphenylmagnesium bromide, and the unknown bromide solution was 2-methylbromobenzene. Calculations showed that the limiting reagent of the Grignard preparation was magnesium and that the experiment had a 23.13 % yield.
Many techniques and skills were developed in this lab. Among them were dehydration, isolation, drying, and distillation. We used all of these techniques to get the product we were looking for. In addition to these experimental techniques we also verified our product via spectroscopy which is a new technique. Using IR spectroscopy we were able to
2. Plan: Each student in a group of three will work to create a reaction with the Benzonitrile Oxide with, cis-stilbene, trans-stilbene, or styrene in an Erlenmyer flask. With this Reaction solution thin layer chromatography will be performed using each reaction solution. The different reactions will then be compared by running co-spot TLC’s. An NMR of the crude products from each reaction will be taken.
The bromination of the alkane was calculated and the overall percent yield was 96.35% with the percent yield with the calculated theoretical yield was 79.85%. The addition reaction was synthesized with a mechanism using 3 steps. The E-Stilbene reacted with pyridinium hydromide perbromide to form the pure (1R, 2S)-stilbene dibromide. One of the two diastereomeric products, the other would be dl(1R,2R + 1S,2S) stilbene dibromide.
The main purpose of this experiment was to study the mechanism of the isomerization of dimethyl maleate to dimethyl fumarate as well as to explore the different properties of enantiomers using (R) and (S) Carvone oils, such as polarimetry and odor. A percent yield was calculated based upon the original amount of dimethyl maleate added to the reaction, and the melting point was also be taken to determine the purity of the final product.
Starting with 8.03 grams of maleic anhydride crystals, the students successfully converted them into two isomers of butenedioic acid. From the experiment, the students learned that maleic acid converts to fumaric acid in the presence of a proton. Little occurred during the reaction between the maleic anhydride and water. The solution remained clear during the heating. Moreover, all the crystals produced during the experiment are white and brittle. Furthermore, the students obtained 6.09 grams of maleic acid, the crystals produced in the first part of the lab and 0.90 grams of fumaric acid, the crystals produced in the second part of the lab. During the melting point test, the crystals of maleic acid begin melting at 121oC and fully melted
The overall purpose of this lab was to see how bonding effects chemical and physical properties. The lab consisted of 6 compounds Dodecanoic Acid, Sodium Chloride, Duodecose, Octadecanoic Acid, Potassium Bromide and Amylose. Using these compounds, tests were conducted on their appearance, solubility in distilled water, conductivity and melting point. There are 3 groups these compounds can be organized into. One group is Dodecanoic Acid and Stearic Acid. Another group is Duodecose and Amylose and the last group is Sodium Chloride and Potassium Bromide. These compounds are put into these groups because of their similar structures and properties.
Ferrocene, 9-fluorenone and acetylferrocene had melting points of 174-175̊C, 83-86̊C, and 83-85̊C, respectively. The mixture after evaporation accounted for roughly 68% of the original mixture. This was mainly due to product loss from keeping only the pure test tubes. Based on the amount of product obtained, unknown #16 consisted of mostly ferrocene, and least of
The precipitated solid was filtered out washed with ice-water three times and further purified by recrystallization with hot ethanol. In addition, purification of product was carried out by passing sample through a short column of silica gel whenever it is necessary. The obtained pure products then examine and confirmed by further characterization using 1H and 13C NMR spectroscopy and elemental analysis. All the melting points of prepared compounds were determined in open capillary tubes and are in corrected. The FT-IR spectra were recorded on a Perkin-Elmer spectrophotometer using KBr pellets.
In this experiment, three unknown alkanes were identified by observing their physical and chemical properties. Alkanes are saturated hydrocarbons. The properties identified were qualitative observations, solubility, mass, fire test, boiling point, and volume, and density. Unknown one was identified as hexane, unknown two as pentane, and unknown three as heptane. The results were as unpredictable but understandable and the properties of the boiling points of the unknowns closely match that of the categories of organic compounds, just not the densities. This led to low confidence that the results are invalid.
The beaker was slowly heated on a hot plate with low stirring until most of the stilbene was dissolved. 0.4 g of pyridinium tribromide was measured and added to the beaker after 5 minutes of heating. Small amounts of ethanol were used to clean the sides of the beaker. The beaker was heated for an additional 10 minutes on low temperature. An ice bath was prepared. The beaker was removed from the hot plate and left to cool to room temperature. Once at room temperature, the beaker was placed in the ice bath for 15 minutes. The solid product was collected through vacuum filtration and the product was weighed and a melting point was taken. Waste was disposed of in the correct waste bins and lab bench was cleaned
In this laboratory project, Compound “E” was identified as N-Phenylsuccinimide. The % yield was 60.5 %. The melting point of both Compound “E” and N-Phenylsuccinimide was 153-154 ⁰C, as verified through experimentation; the official melting point range of N-Phenylsuccinimide is 153-157 ⁰C. The yield of dibromobenzene was 1 gram, and the % yield of dibromobenzene was 69.2%. The purpose of this experiment was to purify an impure compound through recrystallization, and then identify it through measuring the melting point.
After all additional product ceased to form, the reaction mixture was cooled in an ice bath to allow precipitation of benzopinacol. The final product was then filtered off from the solution using a Buchener funnel. Its melting point, yield and infrared spetrum was then obtained.
Suzuki–Miyaura Reaction: Pd-containing catalytic GONs (3 mg) were added to 3 mL of solvent containing aryl halide (1 mmol), phenylboronic acid (2 mmol), base (4 mmol), and tetrabutylammonium bromide (2 mmol). The reaction mixture was magnetically stirred at boiling temperature under Ar. The reaction mixture was cooled to room temperature, and the crude products were purified by column chromatography on 230-400 mesh silica gel using ethyl acetate and hexane (1:10 v/v) as the eluant. The isolated compounds were analyzed by 1H NMR (500 MHz) and 13C NMR (125 MHz), with the chemical shifts reported relative to residual CDCl3 solvent peaks (1H NMR: 0 ppm, 13C NMR: 77.01 ppm) and tetramethylsilane (TMS) as an internal standard. Detailed information for the samples is given in the Supplementary Data.
During this lab the melting point ranges and boiling points were recorded from several substances. Based upon the structures of these various samples certain trends were expected to be followed. For example, with the melting points of pure substances are usually higher than the melting points of impure substances. In this lab the melting point of Benzoic Acid, Salicylic Acid, 3-Hydroxybenzoic Acid, 4–Hydroxybenzoic Acid, and Sulfosalicylic Acid were taken. If we apply the concept of pure substances having higher boiling points, it was expected for substances like 3-Hydroxybenzoic Acid and 4–Hydroxybenzoic Acid to have higher melting points and for