Introduction Elimination reactions are one of many different types of reactions, yet elimination reactions are one of the most common practices to create carbon-carbon π-bonds. Dehydrohalogenation is an example of functional group transformation. In the case of alkyl halides they are transformed into alkenes through dehydrohalogenation (1). The general mechanism for dehydrohalogenation elimination reactions when a strong base is used can be written as: RCHCH_2-X+B:^- → RCH=CH_2+B-H+X:^- [INSERT DRAWING HERE] Bromine is a hazardous chemical that can cause major chemical burns (liquid and gaseous). Gloves and proper laboratory gear should be worn at all times when handling solutions containing bromine. If the bromine does get onto …show more content…
The products obtained from the bromination of alkenes using cis-2-butene and trans-2-butene are dl-stilbene and meso-stilbene. Meso-stilbene and dl-stilbene are diastereomers, thus they have different properties. Because the compounds meso-stilbene and dl-stilbene are diastereomers it makes identifying the major product in the bromination reaction very easy (1). The meso compound is formed after the reaction with the Br2/CH2Cl2 (CH2Cl2 = dichloromethane) occurs. It is called meso because of the placement of the bonds and the stereogenic centers. The major product of the reaction is the meso-stilbene compound. Norbornene is a volatile and smelly substance it should be handled quickly with care and not be removed from the hoods. Sulfuric acid can cause burns if it comes in contact with skin. If contact with skin does occur wash the area with 5% sodium bicarbonate solution. The basic solution if in contact with skin rinse the area with 1% acetic acid solution (1). Acid catalyzed hydration of alkenes produces and alcohol by the addition of water through carbon-carbon π-bonds. In other terms this reaction is the reverse of acid catalyzed dehydration which removes an alcohol. The mechanism for acid catalyzed hydration of alkenes is demonstrated …show more content…
Hydration of norbornene: [INSERT REACTION HERE] The intermediate is: [INSERT REACTION HERE] Equilibrium in the reaction can be shifted towards the formation of the addition product by using sulfuric acid to drive the reaction. Conclusion Advantages of alkene preparation through dehydrohalogenation of alkyl halides under basic conditions are that the reaction will not produce the products formed thermodynamically, only the kinetic products will be collected. Based on the results produced in the laboratory experiment the functional groups in the substrate can be changed by the strength and the amounts of the solvents used. The efficiency of the reactions are as expected. Side reactions that have the possibility of occurring are due to changes in thermodynamics, kinematics, or in the strengths and amounts of the solvents used. References Gilbert, C. John; Martin, F. Stephen. 2011. Experimental Organic Chemistry: A Miniscale and Microscale Approach. 5th Edition. Cengage Learning. pp.
The experiment of Diels-Alder reactions, in particular the furan and maleic anhydride as used in my experiment, observed the exo product as oppose to the exo product. This shows the tendency for the stereochemistry of the Diels-Alder to yield an exo product in preference to the endo product. To determine the stereochemistry, a melt temperature of the product was taken and compared to literature values. The melt temperature for the product was roughly around 113oC, corresponding to the exo Diels-Alder product of furan and maleic anhydride. When compared to the class data of melting ranges, the melting temperature from the reaction was relatively consistent to the majority. Based off this, the assumption can be made that the Diels-Alder prefers
Depending on which face of carbonyl the hydride attacks, the ketone could result in two different diastereomers of product. Since the two ketone faces are nonequivalent, there will be stereo selectivity in reduction which means that one diastereomer will be more prevalent than the other. There are three reduction conditions can be used to reduce the 4-tert-butylcyclohexanone : NaBH4, MPV , and L-selectride. For NaBH4, the hydride attach itself to the carbonyl oxygen to become the hydroxyl group and it more likely from the top because the hydride isn’t blocked by a bulky group (Fig mech prez). Both sodium borohydride and lithium aluminum hydride are less bulky hydride reducing agents so it is expected that they will be able to attack from the top face of the molecule since the bulky tert-butyl group will not hinder the attack. For L-selectride mechanism is similar to NaBH4, the L-selectride is a source of hydride for the carbonyl oxygen but there are bulky groups that block the hydride. Since L-selectride is much larger and bulkier hydride reagent so likely not be able to attack from the top face in the presence of the bulky tert-butyl group (fig 1 and 2 like web) For MPV, the ketone is reduced with aluminum isopropoxide in isopropanol. The carbonyl oxygen attack the aluminum which causes the carbonyl oxygen to have a +1 charge, a hydrogen as
The complete experimental procedure is available in the General Chemistry Laboratory Manual for CSU Bakersfield, CHEM 213, pages 20-22, 24-25. Experimental data are recorded on the attached data pages.
The purpose of the experiment is to study the rate of reaction through varying of concentrations of a catalyst or temperatures with a constant pH, and through the data obtained the rate law, constants, and activation energies can be experimentally determined. The rate law determines how the speed of a reaction occurs thus allowing the study of the overall mechanism formation in reactions. In the general form of the rate law it is A + B C or r=k[A]x[B]y. The rate of reaction can be affected by the concentration such as A and B in the previous equation, order of reactions, and the rate constant with each species in an overall chemical reaction. As a result, the rate law must be determined experimentally. In general, in a multi-step reac...
Nickel is hazardous in case of inhalation, slightly hazardous in case of skin contact (irritant, sensitizer), and of ingestion. May also cause damage to the following organs: kidneys, lungs, liver, and upper respiratory tra...
Michael P. Broadribb, C. (2006). Institution of Chemical Engineers . Retrieved July 26, 2010, from IChemE: http://cms.icheme.org/mainwebsite/resources/document/lpb192pg003.pdf
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 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%).
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
In order to separate the mixture of fluorene, o-toluic acid, and 1, 4-dibromobenzene, the previously learned techniques of extraction and crystallization are needed to perform the experiment. First, 10.0 mL of diethyl ether would be added to the mixture in a centrifuge tube (1) and shaken until the mixture completely dissolved (2). Diethyl ether is the best solvent for dissolving the mixture, because though it is a polar molecule, its ethyl groups make it a nonpolar solvent. The compounds, fluorene and 1, 4-dibromobenzene, are also nonpolar; therefore, it would be easier for it to be dissolved in this organic solvent.
Abstract: This week we experimentally determined the rate constant k for the reaction 2HCl (aq) +Na2S2O3 (aq) → S (s) + SO2 (aq) + H2O (l) + 2NaCl (aq). In order to do this the average reaction time was recorded in seconds during two trials. The data from the experiment shows this reaction is in the first order overall: rate=.47s-1 [HCl]0 [Na2S2O3]1. These findings seem to be consistent with the expected results
Predictions may be made about the suitability of possible catalysts by assuming that the mechanism of catalysis consists of two stages, either of which can be first:
There is no addition of feed or removal of product along the reaction is carried out (Blevins, 20014).
Development of specific ethers has been inactive and fruitful area of investigation in the past few decades.2The strategy of ether catalysis General encompasses synergistic activation of a ethers an electrophile by two or more reactive centers through the combination of a Lewis acid and Lewis base working in concert. Such approach results in high reaction rates and excellent ethers. Hydrogen bonding plays a crucial role in this catalysis. Hydrogen bonding to an electrophile decreases the electron density of this species, activating it toward nucleophilic attack. Recently chemists have begun to appreciate the tremendous potential offered by hydrogen bonding as a tool for electrophile activation in synthetic catalytic systems. In particular, ethers donors have emerged as a broadly applicable class of catalysts for ethers synthesis. An amide unit, the key functional group of peptides, plays an important role in catalyst design and modification. Based on the understanding of different asymmetric catalytic reaction mechanisms, the creation of amide structure-based ether and was realized by rational arrangement of hydrogen-bond networks. According to their model, two water molecules simultaneously establish H-bonds to the carbonyl oxygen of the substrate for optimal transition state stabilization. The concept of explicit double H-bonding activation was no longer restricted to one type of reaction or catalyst, but became a generally applicable principle. The simultaneous donation of two hydrogen bonds has proven to be a highly successful strategy for electrophile activation. Such interactions benefit from increased strength and directionality compared to a single hydrogen bond. Ethers containing double hydrogen bond ethers are capable of directing the assembly of molecules with similar control as