Purpose/Introduction
What reaction was conducted in this experiment and with what reagents? Was there a reason for this reaction beyond just synthesis of product(s)? What techniques were used to purify and identify the product(s) of the reaction?
The purpose of this experiment was to investigate the bromination of trans-cinnamic acid and determine what the isolated products tells us about the possible mechanism. The stereochemistry of the product results from either a syn or anti addition of Br2 to the alkene. Recrystallization using ethanol and water solvent mixture was used to purify the crude product and melting point was implemented in order to see which products were synthesized. The syn addition products (2S, 3S- and 2R, 3R) 2,3-dibromo-3-phenylpropanoic acid have a melting range of 93.5-95 ᵒC. The anti addition products (2S, 3R- and 2R, 3S) 2,3-dibromo-3-phenylpropanoic acid have a melting range of 202-204 ᵒC.
Theory:
Experiment-Specific Questions:
In this experiment you were asked to present three possible mechanisms. Describe those mechanisms here. How will the bromination of trans-cinnamic acid allow you to distinguish between the three possibilities? What would you expect to find in your data in each scenario?
The three possible mechanisms are syn addition, anti addition, and both syn and anti addition. The syn addition is where both bromine atoms are added to the same face of the alkene. The anti addition is where both bromine atoms are added to opposite sides of the alkene. The syn addition mechanism is a concerted reaction since all bonds are made and broken at the same time. The pi bond from the C=C double bond is given to one of the bromine atoms. The Br–Br bond is broken and one of the bromine atoms acqu...
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...ge of 202-204 ᵒC. Therefore, the concluded mechanism was anti addition of bromine to trans-cinnamic acid resulting in (2S, 3R- and 2R, 3S) 2,3-dibromo-3-phenylpropanoic acid (pair of enantiomers) based off the key pieces of data derived from the melting point experimentation. If this experiment were to be conducted again, some possible changes can be to use a greater mass of reagents. This can help lower the chance in having the unreacted substances stuck to the sides of the glassware, consequently lowering the yield. Moreover, the addition of Br2 ideally should be from a fresh batch and free of contaminants; this goes the same for trans cinnamic acid. Having all reagents react in optimal conditions is what further increases the probability of obtaining a higher yield in recrystallized product and a melting point closer to that of the expected product.
When 1-bromobutane is reacted with potassium t-butoxide there is only one product formed, 1-butene. This is because the halide is on a primary carbon thus producing only one product.
In a small reaction tube, the tetraphenylcyclopentadienone (0.110 g, 0.28 mmol) was added into the dimethyl acetylene dicarboxylate (0.1 mL) and nitrobenzene (1 mL) along with a boiling stick. The color of the mixed solution was purple. The solution was then heated to reflux until it turned into a tan color. After the color change has occurred, ethanol (3 mL) was stirred into the small reaction tube. After that, the small reaction tube was placed in an ice bath until the solid was formed at the bottom of the tube. Then, the solution with the precipitate was filtered through vacuum filtration and washed with ethanol. The precipitate then was dried and weighed. The final product was dimethyl tertraphenylpthalate (0.086 g, 0.172mmol, 61.42%).
The percent yield of products that was calculated for this reaction was about 81.2%, fairly less pure than the previous product but still decently pure. A carbon NMR and H NMR were produced and used to identify the inequivalent carbons and hydrogens of the product. There were 9 constitutionally inequivalent carbons and potentially 4,5, or 6 constitutionally inequivalent hydrogens. On the H NMR there are 5 peaks, but at a closer inspection of the product, it seems there is only 4 constitutionally inequivalent hydrogens because of the symmetry held by the product and of this H’s. However, expansion of the peaks around the aromatic region on the NMR show 3 peaks, which was suppose to be only 2 peaks. In between the peaks is a peak from the solvent, xylene, that was used, which may account to for this discrepancy in the NMR. Furthermore, the product may have not been fully dissolved or was contaminated, leading to distortion (a splitting) of the peaks. The 2 peaks further down the spectrum were distinguished from two H’s, HF and HE, based off of shielding affects. The HF was closer to the O, so it experienced more of an up field shift than HE. On the C NMR, there are 9 constitutionally inequivalent carbons. A CNMR Peak Position for Typical Functional Group table was consulted to assign the carbons to their corresponding peaks. The carbonyl carbon, C1, is the farthest up field, while the carbons on the benzene ring are in the 120-140 ppm region. The sp3 hybridized carbon, C2 and C3, are the lowest on the spectrum. This reaction verifies the statement, ”Measurements have shown that while naphthalene and benzene both are considered especially stable due to their aromaticity, benzene is significantly more stable than naphthalene.” As seen in the reaction, the benzene ring is left untouched and only the naphthalene is involved in the reaction with maleic
Enantiomers, a type of isomer, are non-superimposable, mirror images of each other. Diasteriomers, another type of isomer, are non-superimposable, non-mirror images of each other. Dimethyl maleate and dimethyl fumarate are diasteriomers, as they are not mirror images but instead vary in the orientation of the carbomethoxy groups around the double bond. Dimethyl maleate is the cis-isomer because both groups are on the same side and dimethyl fumarate is the trans-isomer because the two groups are on opposite sides. A bromine free radical mechanism was required for this conversion. First, energy from light is required to create two bromine free radicals from Br2. Then one of the free radicals attacks the double bond in dimethyl maleate, breaking it and creating a carbon radical on the other carbon. The bond then rotates and reforms, freeing the bromine radical and creating the trans-isomer, dimethyl fumarate. Bromine in this reaction is acting as a catalyst in this reaction and then cyclohexane is added at the end to neutralize the bromine free radicals. The activation reaction of the radical reaction is lower than the activation energy of the addition reaction, which is why it occurred more quickly. This reaction was successful because the percent yield was 67.1%, which is greater that 65%. It also demonstrated the expected principles, as the reaction did not occur without the presence of both light and bromine. The dimethyl fumarate had a measured boiling point of 100C to 103C, which is extremely close to the expected boiling point of 102C to
Objective: The objective of the experiment is to determine what factors cause a change in speed of a reaction. It is also to decide if the change is correlated with the balanced equation of the reaction and, therefore, predictable. To obtain a reaction, permanganate, MnO_4^(1-), must be reduced by oxalic acid, C_2 O_4 H_2. The balanced equation for the reaction is:
2-ethyl-1,3-hexanediol. The molecular weight of this compound is 146.2g/mol. It is converted into 2-ethyl-1-hydroxyhexan-3-one. This compounds molecular weight is 144.2g/mol. This gives a theoretical yield of .63 grams. My actual yield was .42 grams. Therefore, my percent yield was 67%. This was one of my highest yields yet. I felt that this was a good yield because part of this experiment is an equilibrium reaction. Hypochlorite must be used in excess to push the reaction to the right. Also, there were better ways to do this experiment where higher yields could have been produced. For example PCC could have been used. However, because of its toxic properties, its use is restricted. The purpose of this experiment was to determine which of the 3 compounds was formed from the starting material. The third compound was the oxidation of both alcohols. This could not have been my product because of the results of my IR. I had a broad large absorption is the range of 3200 to 3500 wavenumbers. This indicates the presence of an alcohol. If my compound had been fully oxidized then there would be no such alcohol present. Also, because of my IR, I know that my compound was one of the other 2 compounds because of the strong sharp absorption at 1705 wavenumbers. This indicates the presence of a carbonyl. Also, my 2,4-DNP test was positive. Therefore I had to prove which of the two compounds my final product was. The first was the oxidation of the primary alcohol, forming an aldehyde and a secondary alcohol. This could not have been my product because the Tollen’s test. My test was negative indicating no such aldehyde. Also, the textbook states that aldehydes show 2 characteristic absorption’s in the range of 2720-2820 wavenumbers. No such absorption’s were present in my sample. Therefore my final product was the oxidation of the secondary alcohol. My final product had a primary alcohol and a secondary ketone
...form 〖PbCrO〗_4 and then process it through a filter. After filtering the 〖PbCrO〗_4 I had to dry the 〖PbCrO〗_4 residue in the drying oven for 30 minutes at 80℃. Then let it cool for 5 minutes and weigh it and finally make a few calculations to obtain the theoretical, actual, and percent yields of 〖PbCrO〗_4. I was able to fulfill the experiment because I obtained all the answers to the equations in an accurate amount. I believe this experiment was a success due to my hypothesis of, If physical methods are used to separate 〖 PbCrO〗_4 precipitate from the reaction mixture then I can successfully calculate the theoretical, actual, and percent yields, being correct.
Discussion The reaction of (-)-α-phellandrene, 1, and maleic anhydride, 2, gave a Diels-Alder adduct, 4,7-ethanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-5-methyl-8-(1-methylethyl), 3, this reaction gave white crystals in a yield of 2.64 g (37.56%). Both hydrogen and carbon NMR as well as NOESY, COSY and HSQC spectrum were used to prove that 3 had formed. These spectroscopic techniques also aided in the identification of whether the process was attack via the top of bottom face, as well as if this reaction was via the endo or exo process. These possible attacks give rise to four possible products, however, in reality due to steric interactions and electronics only one product is formed.
The goal of this lab is to exemplify a standard method for making alkyne groups in two main steps: adding bromine to alkene groups, and followed by heating the product with a strong base to eliminate H and Br from C. Then, in order to purify the product obtained, recrystallization method is used with ethanol and water. Lastly, the melting point and IR spectrum are used to determine the purity of diphenylacetylene.
Benzyl bromide, an unknown nucleophile and sodium hydroxide was synthesized to form a benzyl ether product. This product was purified and analyzed to find the unknown in the compound. A condenser and heat reflux was used to prevent reagents from escaping. Then the solid product was vacuum filtered.
In the experiment “ Talking to plants “ from Mythbusters, potential problems include the use of greenhouses with no sound insulation, a non-homogeneous location and the use of only one specie to infer on a population. In another scientific study, researchers chose to use “ a noiseless growth chamber to prevent any effects from extraneous noise “ and the use “ growth chambers under continuous light at 28 c and 65-75% relative humidity “ in order to maintain a homogeneous location for all plants during the experiment (Jeong et al., 2008) . This helped further explain the findings because with the use of noiseless chambers you can assure that the only noise that the plant was receiving was the one given in the treatment and a valid conclusion
Ensure gloves are worn at all times when handling strong acids and bases within the experiment of the preparation of benzocaine. 4-aminobenzoic acid (3.0g, 0.022 moles) was suspended into a dry round-bottomed flask (100cm3) followed by methylated sprits (20 cm3). Taking extra care the concentrated sulphuric acid of (3.0 cm3, 0.031 moles) was added. Immediately after the condenser was fitted on, and the components in the flask were swirled gently to mix components. It should be ensured that the reactants of the concentrated sulphuric acid and the 4-aminobenzoic acid were not clustered in the ground glass joint between the condenser itself and the flask. In order to heat the mixture to a boiling point, a heating mantle was used and then further left for gently refluxing for a constituent time of forty minutes. After the duration of the consistent forty minutes the rou...
During a time of moral and civil unrest, Herbert Hoover, the 31st president of the United States attempted a “great social and economic experiment” that led to the prohibition of alcohol. On January 19, 1920 the US enacted the 18th amendment and set forth into the Prohibition Era. This amendment outlawed the “manufacture, sale or transportation of intoxicating liquors”. Americans later coined the term the “noble experiment” to describe this event in our national history. Unfortunately, the events that took place during this decade were anything but noble. After much backlash and dire consequence, President Theodore Roosevelt would end prohibition by proposing the 21st Amendment to the Constitution that appealed
n hypothesis of the experiment is that the group containing four members will perform better than the group containing two members. This is the foundation from which we have conducted our experiment.
The reaction mixture was then cooled down to room temperature and was not disturbed during the cooling process. Crystals were formed and then the beaker was placed into an ice-water bath until the liquid had thickened into a semi-solid