The purpose of this experiment is to examine the reactivity of different compounds. To accomplish this, different types of benzene (aniline, acetanilide, phenol, or anisole) will be brominated. The reactivity and activation strength will determine of the compound is polyhalogenated, or monohalogenated. In this experiment it is to be predicted in which order the reaction substitution(s) will occur and the reactivity order of each of the benzene compounds. The product will then be analyzed and identified by recrystalling and comparing the melting point of isolated product to literature values. Electrophilic aromatic substitution (EAS) is the introduction of a functional group to a benzene ring. In the reaction, a …show more content…
hydrogen is replaced with an electrophile. An electrophile is a reagent that is “a lover of electrons” and is attracted to electrons. The speed of a electrophilic aromatic substitution is determined by the substituent attached to the benzene ring. The effect of the substituent group determines if the ring is activating or deactivating. This experiment only uses activating rings; activating substituents help to stabilize the carbonic intermediate that is formed during substitution, thus making is easier to introduce new or multiple substituents to the ring. Ring activating substituents are electron donating and make the benzene more electron rich. Activating substituents direct the incoming substituents into the ortho, para positions. Ortho (1,2 positions). Para ( 1,4 positions). In the ortho and para positions, the extra resonance structures help to stabilize the carbocation intermediate. Mechanism: (Attached to the Back) The mechanism includes two steps. In the first step, the pi electrons from the benzene rings attack the electrophile. Because the benzene rings is stable, there is a high energy of activation making this is the rate determining step. This step is where the carbocation intermediate is formed. In the second step, a base attacks the carbocation intermediate, and a proton is lost where the electrophile attacked the ring. The electrons are used to reform the pi bond. Data: Grams Melting Ranges grams of Phenol used: 1mmol = .001 mol 1mol = 0.0941g 94.1 g phenol 0.001 mol Class Results: The hypothesis was that the reactivity of the three compounds was aniline > phenol > anise > acetonilide.
The hypothesis expected that aniline and phenol would be tri-substituted, and anisole an acetanilide would be mono-substituted and have a bromine in the para position, because the para position is favored over the ortho position because of sterics. Results after the experiment were: phenol > aniline > acetanilide. Anisole was not applicable because the experiment was not ran during class and that data was not provided. The results for aniline were one group claiming 2,6 dibromoaniline and two groups claiming 2,4 dibromoanaline. 2,4 dibromoanaline seems more probable because it is preferred to have substituents spaced out on an aromatic ring, for less tension between substrates. The conclusion with phenol was that it was trisubstituted 2,4,6 tribromophenol. Although there are two melting points, it is the same product that was being analyzed, because only one group could correctly brominate phenol. The temperature difference is attributed to two different mel-temps being used, causing two different temperatures. The results for acetanilide, were that all three groups concluded that 4-bromoacetanailde was the product. This is predictable because acetanailde is a bulky substrate. Compounds favor that bulky substituents only attach in the para
position. The conclusion drawn as to why phenol is more substituted than aniline is because the reaction takes place in an acidic solution (acetic acid was used); phenol should undergo EAS faster than aniline in an acidic solution. Phenol is acidic and therefore will not be deprotinated in an acidic solution. Unlike aniline which is a weak base, can accept protons and become positively charged, therefore is not as activating than phenol. To test this, completing the experiment again in a more neutral medium could prove that aniline is actually more activating than phenol.
The competing enantioselective conversion method uses each enantiomer of a kinetic resolution reagent, in this case R-HBTM and S-HBTM, in separate and parallel reactions, where the stereochemistry of the secondary alcohol is determined by the rate of the reactions. When using the CEC method, the enantiomer of the secondary alcohol will react with one enantiomer of the HBTM acyl-transfer catalyst faster than with the other HBTM enantiomer. The mnemonic that identifies the absolute configuration of the secondary alcohol is as follows: if the reaction is faster with the S-HBTM, then the secondary alcohol has the R-configuration. In contrast, if the reaction is faster with the R-HBTM, then the secondary alcohol has the S-configuration. Thin layer chromatography will be used to discover which enantiomer of HBTM reacts faster with the unknown secondary alcohol. The fast reaction corresponds to a higher Rf spot (the ester) with a greater density and a slower reaction corresponds to a lower Rf spot with high de...
The goal of this experiment is to determine which products are formed from elimination reactions that occur in the dehydration of an alcohol under acidic and basic conditions. The process utilized is the acid-catalyzed dehydration of a secondary and primary alcohol, 1-butanol and 2-butanol, and the base-induced dehydrobromination of a secondary and primary bromide, 1-bromobutane and 2-bromobutane. The different products formed form each of these reactions will be analyzed using gas chromatography, which helps understand stereochemistry and regioselectivity of each product formed.
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 spots moved 3.8cm, 2.3cm, 2.1cm, 1.8cm, and 2.5 cm, for the methyl benzoate, crude product, mother liquor, recrystallized product, and isomeric mixture, respectively. The Rf values were determined to be.475,.2875,.2625,.225, and.3125, for the methyl benzoate, crude product, mother liquor, recrystallized product, and isomeric mixture, respectively. Electron releasing groups (ERG) activate electrophilic substitution, and make the ortho and para positions negative, and are called ortho para directors. In these reactions, the ortho and para products will be created in a much greater abundance. Electron Withdrawing groups (EWG) make the ortho and para positions positive.
The goal of this two week lab was to examine the stereochemistry of the oxidation-reduction interconversion of 4-tert-butylcyclohexanol and 4-tert-butylcyclohexanone. The purpose of first week was to explore the oxidation of an alcohol to a ketone and see how the reduction of the ketone will affect the stereoselectivity. The purpose of first week is to oxidize the alcohol, 4-tert-butylcyclohexanol, to ketone just so that it can be reduced back into the alcohol to see how OH will react. The purpose of second week was to reduce 4-tert-butylcyclohexanol from first week and determine the effect of the product's diastereoselectivity by performing reduction procedures using sodium borohydride The chemicals for this lab are sodium hypochlorite, 4-tert-butylcyclohexanone
The primary goal of this laboratory project was to identify an unknown compound and determine its chemical and physical properties. First the appearance, odor, solubility, and conductivity of the compound were observed and measured so that they could be compared to those of known compounds. Then the cation present in the compound was identified using the flame test. The identity of the anion present in the compound was deduced through a series of chemical tests (Cooper, 2009).
The positive charge on the phosphorus atom is a strong EWG (electron-withdrawing group), which will trigger the adjacent carbon as a weak acid. 5 Very strong bases are required for deprotonation such as an alkyl lithium, however in this experiment 50% sodium hydroxide was used as reiterated. Lastly, the reaction between ylide and aldehyde/ketone produces alkene. (Eq. 1) As shown in equation 2, the reaction between the phosphonium salt and the sodium hydroxide produces the ylide/carbanion that is stabilized due to the positive charge on phosphorus and the conjugation that occurs in the benzene ring as shown by the structure B in equation 2.
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.
A weak peak was at a position between 1600-1620 cm-1 can also be seem in the IR, which was likely to be aromatic C=C functional group that was from two benzene rings attached to alkynes. On the other hand, the IR spectrum of the experimental diphenylacetylene resulted in 4 peaks. The first peak was strong and broad at the position of 3359.26 cm-1, which was most likely to be OH bond. The OH bond appeared in the spectrum because of the residue left from ethanol that was used to clean the product at the end of recrystallization process. It might also be from the water that was trapped in the crystal since the solution was put in ice bath during the recrystallization process. The second peak was weak, but sharp. It was at the position of 3062.93 cm-1, which indicated that C-H (sp2) was presence in the compound. The group was likely from the C-H bonds in the benzene ring attached to the alkyne. The remaining peaks were weak and at positions of 1637.48 and 1599.15 cm-1, respectively. This showed that the compound had aromatic C=C function groups, which was from the benzene rings. Overall, by looking at the functional groups presented in the compound, one can assume that the compound consisted of diphenylacetelene and ethanol or
The product was recrystallized to purify it and the unknown filtrate and nucleophile was determined by taking the melting points and performing TLC. Nucleophilic substitution reactions have a nucleophile (electron pair donor) and an sp3 electrophile (electron pair acceptor) with an attached leaving group. This experiment was a Williamson ether synthesis usually SN2, with an alkoxide and an alkyl halide. Conditions are favored with a strong nucleophile, good leaving group, and a polar aprotic solvent.
An elements¡¦ reaction to certain substances may be predicted by its placement on the Periodic Table of Elements. Across a period, an element on the left will react with more vigor than one on the right, of the same period. Vertically, as elements are sectioned into groups, the reaction of each element increases as you move down in the same group. With this in mind, the reactions of the substances involved in this experiment may be hypothesized, observed, and validated.
The purpose of the experiment was to study the kinetics of the hydrolysis of ester, p-nitrophenyl acetate (NPA) that is catalyzed by the buffer imidazole (Im). In terms of kinetics, specifically speaking, the rate of reaction as determined by the concentration, reaction orders, and rate constant with each species in a chemical reaction. By using the concentration of the catalyst and the temperature, the overall reaction rate was determined. The rate constants of K0, Kobs, and Kcat can be derived via the plotting of the absorbtion at 400nm of p-nitrophenol vs. the concentration of the catalyst imidazole. Lastly, the free energy of activation, ΔGǂ, that is necessary to force the reactant’s transformation of the reactants to the transition state structure will be determined by using the equation ΔGǂ = ΔHǂ – TΔSǂ derived from the Eyring plot.
When benzoic acid paired with 1.0 M NaOH, it was observed that both compounds were soluble. Upon the addition of 6.0 M HCl into this solution, benzoic acid became insoluble. Benzoic acid was also insoluble in 1.0 M HCl. Ethyl 4-aminobenzoate was found to be insoluble in 1.0 M NaOH and soluble in 1.0 M HCl. But then, after adding 6.0 M NaOH into the test tube C (mixture of ethyl 4-aminobenzoate and 1.0 M HCl), a white powdery solid (undissolved compound) was formed. These demonstrate that both the acid and base became more soluble when they were ionized and less soluble when they were
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...
The aim of this experiment was to investigate the affect of the use of a catalyst and temperature on the rate of reaction while keeping all the other factors that affect the reaction rate constant.