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Nucleophilic Substitution Reaction Lab Report

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Conducting Results from Various Substitution Reactions that Contain Alcohol Sophia Gruszczyk*, Riley Clark Department of Chemistry and Chemical Biology, IUPUI, 402 N. Blackford St., Indianapolis, IN 46202. segruszc@iu.edu The purpose of this experiment was to determine the structure of a specific product(s) from a given starting material. The reaction that was tested was that of substitution reactions, whether it was SN1 or SN2. Reaction 1 is an SN2 reaction because of the presence of a strong nucleophile and the solvent being polar aprotic. For this reaction, there is only going to be one product which is (3-bromopropyl) benzene. Reaction 3 favors SN1. Since the solvent is polar protic, there is a weak nucleophile, and there is a secondary …show more content…

One of the ways they can do this is through substitution reactions. There are two different types of substitution reactions, SN1 and SN2. Substitution reactions are when one atom or ion is substituted for another. An SN1 reaction is a unimolecular, nucleophilic substitution that is 1st order. However, an SN2 reaction is a bimolecular, nucleophilic substitution that is 2nd order. Both reactions have key components that make each easily identifiable. These things to look out for are the nucleophile, which is a Lewis base that donates electrons, and the electrophile, which is a Lewis acid that accepts electrons and carries the leaving group. Alcohols react with substances like HCl and HBr during substitution reactions because alcohol is not a good leaving group. Determining if the reaction will be SN1 or SN2 is based on the structure of the alcohol and which way the carbocation forms. The solvent also plays a role in what the product will form. If there is a polar aprotic solvent, the reaction will be SN1 and will produce a different product than if a polar aprotic solvent was used, which will be an SN2 reaction. All these components will in turn affect what the final product or products are, and examining the products will aid in confirming if the reaction aligns with being SN1 or SN2. Using the information gathered allows scientists to better identify …show more content…

The OH group is not a good leaving group, so it needs to be protonated with the H2SO4. This will allow water to become the leaving group. When the water leaves, a primary carbocation is produced and only SN2 reactions occur with a primary carbocation and a polar aprotic solvent. The bromine will come and attack the negative charge, the loss of the leaving group leaves on the carbon, forming the desired product. Aromatic rings have a high boiling point, so it was important when running this experiment to carefully watch the reaction so that the solution was not going to burn. This would have resulted in the loss of essential products. Since there is a high activation energy for this reaction, it is necessary to heat using reflux. Heating with reflux also makes it important to be wary of not burning/losing any of the product. The IR appears to be correct as there is no OH peak around 3500 cm-1. TLC was also run for this experiment and showed that the alcohol did not travel, however, the final product did. This indicates that there was a change. When running the GC, there are no peaks for a product, only the acetone. The 1H NMR appears to be correct based on the data. Synthesis of Scheme 2, which has a secondary alcohol, yielding the products and byproducts presented after reflux with hydrochloric acid and zinc

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The other points show some possible errors due to the lack of sharpness and length at the peak near 3000. Conclusion Our results showed some possible errors that might have occurred during the reflux. The lack of OH shows a right step towards the production of the Isopentyl Acetate since during that procedure the alcohol group is converted into a carbonyl group (ester).

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The product obtained was (2S, 3R)-2, 3-dibromo-3-phenylpropanoic acid and (2R, 3S)-2, 3-dibromo-3-phenylpropanoic acid, which are enantiomers. This was determined through melting point analysis. The melting point range for the product was 198 to 202 degrees Celsius, which is a lot close to the given melting point of the anti-addition product, 202-204 degrees Celsius. The given melting point range was 93.5-95 degrees Celsius. Furthermore, the syn-addition product is unlikely and difficult to produce due to stereochemistry selectivity.

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Introduction The bromination of cyclohexene is a classical organic chemistry experiment designed to elucidate the addition of bromine to alkenes. This reaction entails the addition of an electrophilic electron promoter across a carbon-carbon double bond, and the formation of vicinal dibromide. Scheme 1 indicates the net reaction. During the process of the experiment, different analytic methods were implemented to distinguish the reaction product, such as gas chromatography (GC), thin layer chromatography (TLC), and infrared (IR) spectroscopy. Scheme 1: Net Reaction Scheme for the Bromination of Cyclohexene Results and Discussion Component Molecular Weight Mass (g) Volume (mL) Density Boiling Point (°C)

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TLC was used to identify the actual unknown product as well as other products/reactants present in the filtered solution. The procedure was conducted by placing a TLC plate in a developing chamber that is filled with a small amount of solvent. The solvent cannot be too polar because it will cause spotted compounds on the TLC plate to rise up too fast, while a very non-polar solvent will not allow the spots to move. The polarity of the spots also determines how far it moves on the plate; non-polar spots are higher than polar ones. After spots on the TLC form, the Rf values are calculated and used to analyze the similarity of the compounds.

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This supports the isolated product is majority made of the desired product and is largely pure. Mass spectrometry of the crude product shows the molecular ion peak is 162.1, which is the largest fragment in the mass spectrum (Figure 4) and corresponds to the molecular weight of methyl trans-cinnamate (Table 1). The base peak is 131, inferring the fragment lost is 31 m/z in size. This 31 m/z matches the OCH3 fragment of the ester, and would not result from a trans-cinnamic acid. This is evidence the product was successfully

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Nevertheless, the IR spectrum shows that the concentration of Diethyl Ether in the final product is minimal. The reference for the product described two quartet peaks at around 4.0-4.5 (1), which were both seen in our NMR at 3.9 and 4.05 respectively, with integrations of around 2 (Appendix 6). These peaks correspond to the hydrogens in the carbon in between the methyl and the oxygen in the ethyl ester. At around 6-7.5. Two doublet peaks were expected to be present at 6-7.5.

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The purpose of this experiment was to learn about the electrophilic aromatic substitution reactions that take place on benzene, and how the presence of substituents in the ring affect the orientation of the incoming electrophile. Using acetanilide, as the starting material, glacial acetic acid, sulfuric acid, and nitric acid were mixed and stirred to produce p-nitroacetanilide. In a 125 mL Erlenmeyer flask, 3.305 g of acetanilide were allowed to mix with 5.0 mL of glacial acetic acid. This mixture was warmed in a hot plate with constantly stirring at a lukewarm temperature so as to avoid excess heating. If this happens, the mixture boils and it would be necessary to start the experiment all over again.

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Introduction In the presence of a good electrophile, an organic aromatic reactant in specific conditions is likely to undergo a chemical reaction, namely, electrophilic aromatic substitution. An electrophilic aromatic substitution involves the substitution of an unsaturated bond in an aromatic ring with an electrophile (E), to form an arenium ion or sigma complex (-C+-CEH-). Deprotonation at the arenium ion will result in the reformation of the unsaturated bond to preserve stability and the molecule's aromacity.

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Abstract: The purpose of this paper is to inform the reader how to determine SN1 and SN2 reactions. Introduction: Substitution reactions are considered as SN1 or SN2 both consisting of nucleophiles. Substitution reactions that are SN2 consist of 2 reactants and two new products. In SN1 reactions consist of a unimolecular process.

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Nucleophilic substitutions involve a reaction between an electron pair donor with an electron pair acceptor. The second type of nucleophilic substitution is called second-order nucleophilic substitution (Sn2). This experiment involves an Sn1 mechanism only. This reaction is considered

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The general mechanism for EAS occurs in two step series. The first step, which is the rate-determining step, the benzene ring forms a sigma-bond to the aromatic ring, forming an intermediate structure. Thenafter, the proton is removed, forming the substituted aromatic ring. The product of the reaction is affected by the nucleophilic compound’s substituent and the site where the electrophilic substitution will occur.

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There is a very broad substrate-catalyst tolerance and a very broad temperature range that this reaction can operate under (1). The carbon - carbon bond forming capabilities of this reaction is one of the most important outcomes. Accompanying the carbon-carbon bonds this reaction produces, this reaction also shows very high regio- , stereo- , and chemo- , selectivity (1). In addition there are three chemo specific functional groups common to this reaction. Hydroxy, alkene, and electron withdrawing groups (2).

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Additionally, I compared IR spectra I obtained to official IR spectra for para-bromoaniline and 4-bromoacetanilide and they had the same important peaks. Between the two weeks, the reaction time was not very different and was about 15 minutes. The combination of data from TLC, IR, and melting point were able to help me asses the identity of my unknown product, and this the importance of characterization in

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In this experiment, two alcohols, 1-propanol and 2-propanol, were oxidized through combining each with an excess amount of chromic acid solution. The purpose for conducting this experiment was to determine the reaction rate constant at which aldehydes and ketones formed from the respective oxidation of 1-propanol and 2-propanol. From this value, the half-life of the alcohol during the reaction could be derived. The progress of the reaction was tracked through the color change of the solution through use of a spectrophotometer. The first 6 minutes of absorbance of each alcohol’s oxidation were graphed.

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Once the phenol disappeared in the TLC product lane and became fainter in the co-spot lane it became clear that the reaction was at completion. The reaction mixture was then purified using column

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