The Diels-Alder Reaction is an addition reaction between a 1,3-diene and a dienophile. In this reaction, furan, the diene, reacted with maleic anhydride, the dienophile, to form exo-7-oxabicyclo[2.2.1]hept-anhydride, the adduct. The adduct was recovered via vacuum filtration, and the melting point, 1H-NMR and 12C-NMR Spectroscopy was obtained. This Diels-Alder Reaction yielded an exo adduct as opposed to an endo product.
In more detail, the Diels-Alder reaction is the reaction in which the dienophile adds to the alkenes on the diene. The reaction forms a new 6-membered ring and new C-C sigma bonds. The reaction involves breaking 3 pi bonds, and forming 2 new C-C sigma bonds and one new C=C double bond. The reaction is concerted, meaning all
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In general, the diene is the compound with 2 double bonds(1,3-diene) and can only react when it adopts a s-cis confirmation. A s-cis confirmation refers to the position of the double bonds around the sigma bonds, where the double bonds should be on the same side or “cis” to the sigma. A diene in the s-trans confirmation will not react. For example, the diene in this experiment, furan, was in a s-cis confirmation or else it would not have been able to …show more content…
The 13C NMR Spectrum reveals the chemical environments of the C-H bonds. In this experiment, the carbons were assigned a number, from C1 to C4. C4 appeared the most downfield because it was the most deshielded because it is double bonded directly to an O and thus the O pulls the most on electron density. C3 is the most upfield because it is not bonded directly to any electron withdrawing groups or electronegative atom. C1 is the second most deshielded because this carbon is involved in a double bond which draws electron density. C2 appears second most upfield because this carbon is single bonded to an oxygen, but it is not as electron pulling as C4 or C1 that is double
The objective of this lab was to create a ketone through an oxidation reaction using a using a secondary alcohol and oxidizing agent in order to use that ketone in a reduction reaction with a specific reducing agent to determine the affect of that reducing agent on the diastereoselectivity of the product. In the first part of this experiment, 4-tert-butylcyclohexanol was reacted with NaOCl, an oxidizing agent, and acetic acid to form 4-tert-butylcyclohexanone. In the second part of this experiment, 4-tert-butylcyclohexanone was reacted with a reducing agent, either NaBH4 in EtOH or Al(OiPr)3 in iPrOH, to form the product 4-tert-butylcyclohexanol. 1H NMR spectroscopy was used to determine the cis:trans ratio of the OH relative to the tert-butyl group in the product formed from the reduction reaction with each reducing agent. Thin-layer chromatography was used in both the oxidation and reduction steps to ensure that each reaction ran to completion.
Diels-Alder Reaction Objective: The objective of this experiment is to demonstrate a typical Diels-Alder reaction by reacting anthracene (diene) with maleic anhydride (dienophile) to produce 9,10-dihydroanthracene-9,10-α,β-succinc acid anhydride, the product. Scheme 1. Cycloaddition through the Diels-Alder Reaction1 Experimental: Anthracene (1.00 g, 5.61 x 10-3 mol), maleic anhydride, (0.75 g, 7.65 x 10-3 mol), and xylene (5.0 mL) were combined in a 10 mL long-necked, round-bottomed flask. A stir bar was added and an empty distillation column was attached to the flask to function as an air condenser. The mixture was refluxed for 40 minutes over a sand bath, ensuring the temperature was monitored to prevent the reflux ring from surpassing the
The goal of this experiment is to study the most precise way of measuring molecular bond lengths and introduction to computational software used for studying molecular properties. This is of interest in that the instrument to being used, a Fourier-transform infrared (FT-IR) spectrometer, can measure the vibrational and rotational transitions of the fundamental and first overtone of CO. Through this experiment the objective is to collect data from the aforementioned instrument in order to determine vibrational and rotational spectroscopic constants and CO’s bond length, then to
Objective: The objective of this lab is to observe the synthesis of 1-bromobutane in an SN2 reaction, to see how a primary alky halide reacts with an alcohol.
A chemical reaction is when substances (reactants) change into other substances (products). The five general types of chemical reactions are synthesis (also known as direct combination), decomposition, single replacement (also known as single displacement), double replacement (also known as double displacement), and combustion. In this lab, the five general types of chemical reactions were conducted and observations were taken before, during, and after the reaction. Then the reactants and observations were used to determine the products to form a balanced chemical equation. The purpose of this lab was to learn and answer the question: How can observations be used to determine the identity of substances produced in a chemical reaction?
The Diels-Alder reaction was discovered and named after the Nobel Prize winning scientists Kurt Alder and Otto Diels in 1928. Such a reaction occurs when a diene with two adjacent double bonds is mixed with a dienophile consisting of a double bond in order to create a cyclohexene. The diene must be in the s-cis conformation in order for the electron transfer to engage correctly. If the diene in question is in s-trans conformation then the access to the molecules is limited, thus, no reaction can occur. The dienophile we used was maleic anhydride. Maleic anhydride possesses high electron withdrawing characteristics which caused a very quick reaction. The reaction will
In the formation of stilbene dibromide, there are three possible products. The first is meso-stilbene dibromide in which the bromines are on opposite sides of the former double bond. The other two products, d-stilbene dibromide and L-stilbene dibromide, are enantiomers with the two bromines on the same side of the former double bond. As enantiomers, d-stilbene dibromide and L-stilbene dibromide are non-superimposable mirror images of each other. Meso-stilbene dibromide makes up 90% of the yield of this reaction, while d-stilbene dibromide and L-stilbene dibromide make up only 10%.
In order to generate a bicyclic lactone in this experiment, a Diels-Alder adduct was produced. The bicyclic lactone to be generated was cis-1,3,3a,4,5,7a-Hexahydro-5-methyl-3-oxo-4-isobenzofuran-carboxylic Acid and was produced using a Diels-Alder reaction. The product was also analyzed quantitatively using percent yield. To prepare the Diels-Alder adduct 0.40 g of 2,4-hexadien-1-ol was added to a flask, then 5.00 mL of toluene and 0.40 g of maleic anhydride were added to the flask in that order. The mixture was warmed and stirred to induce a reaction. The reaction progress was monitored using a TLC plate with 30:70 hexane used as the mobile phase and silica gel as the stationary phase. The TLC plate revealed a new spot for the crude product, indicating the reaction had begun.
These triple bonds are created by overlapping two pairs of p-orbitals that create a right angle on adjacent sp-hybridized carbon atoms. Two successive elimination reactions are used to prepare alkynes in a manner like the creation of double bonds. The first elimination reaction produces a double bond and the second creates the triple bond. These reactions are done using a strong base and heat.
6. Purpose: to clarify the mechanism for the cycloaddition reaction between benzonitrile oxide and an alkene, and to test the regiochemistry of the reaction between benzonitrile oxide and styrene; to purify the crude product of either trans-stilbene, cis-stilbene, or styrene reaction.
The purpose of this experiment is to examine the reactivities of various alkyl halides under both SN2 and SN1 reaction conditions. The alkyl halides will be examined based on the substrate types and solvent the reaction takes place in.
According to the mechanisms suggested before Chauvin, the only possible products are ethylene and tetradeuteroethylene—along with cyclohexene. The pairwise participation of the carbon atoms in the mechanism prevents the formation of 1,2-dideuteroethylene. However, according to the Chauvin mechanism all three ethylene products should be formed and in a statistical ratio 1:2:1.
In the weeks reading, “Death of a salesman”, writing by Arthur Miller, created a scene in which plots a salesman with many problems. The technology that was presented was around 1949 in which no modern computers or emails existed. A salesman had to travel by car on his own to create income for his family and although many salesmen had family to support in cities where they would have to leave for weeks at a time, the salesman would always find time for his or her family. The salesman name is Willy in which his family is mentioned throughout the play. At the beginning his wife Linda, is always very supportive of his views towards his sales career
That the more stable alkene trans-2-butene, is the major product at approximately 82%. While, the two minor products would be 1-butene at 14%, and cis-2-butene at only approximately 4%.
Furthermore, in this experiment we learned that NMR takes advantage of the magnetic properties of the 1H and 13C nuclei. We are not concerned with 12C because it does not have a magnetic