Arenes 5. Introduction In this experiment, the relative rates of free-radical chain bromination where determined. Five arenes were used for this comparison along with two controls for each set. One set was kept in the dark while the other was put under light. This allowed for better observation of the reactions, as the light set would proceed fast to show which arenes reacted slowest, while the dark set would proceed slowly to show relative differences between the faster reacting arenes. The time it took for the arenes to react was recorded to determine the relative rates of the reactions. 6. Data and Results The five arenes used for this experiment were toluene, ethylbenzene, tert-butylbenzene, cyclohexane, and methylcyclohexane. All solutions were a dark orange right after the addition of bromine. Toluene had 1º benzylic and 2º aromatic hydrogens. Ethylbenzene had 2º benzylic, 1º aliphatic, and 2º aromatic hydrogens. tert-butylbenzene had 1º aliphatic and 2º aromatic hydrogens. Cyclohexane had 2º aliphatic hydrogens and methylcyclohexane had 1º, 2º, and 3º aliphatic hydrogens. In the set that was exposed to light, Ethylbenzene was the first to react. It turned from a dark orange color to a colorless liquid. Next, toluene turned colorless. After that, none of the other solutions turned colorless. However, …show more content…
More specifically, secondary benzylic hydrogens are more reactive than primary benzylic hydrogens, which are more reactive than tertiary aliphatic hydrogens and so on. This is due to the fact that secondary benzylic hydrogens are more accessible than primary benzylic hydrogens due to less steric hindrance. With less steric hindrance, the transition states formed from secondary benzylic hydrogens are more stable than transition states formed from primary benzylic hydrogens and therefore the resulting products are more
In radical halogenations lab 1-chlorobutane and 5% sodium hypochlorite solution was mixed in a vial and put through tests to give a product that can then be analyzed using gas chromatography. This experiment was performed to show how a radical hydrogenation reaction works with alkanes. Four isomers were attained and then relative reactivity rate was calculated. 1,1-dichlorobutane had 2.5% per Hydrogen; 1,2-dichlorobutane had 10%; 1,3-dichlorobutane had 23%; and 1,4-dichlorobutane had 9.34% per Hydrogen.
The purpose of this experiment was to practice the functional group transformation procedure. The process of the experiment included the dehydration of 2-methylcyclohexanol in the presence of phosphoric acid and heat. The products that were formed from the reaction were 1-methylcyclohexene and 3-methylcyclohexene. The mass of the final product solution was 0.502g with a percent yield of 18.7% and a boiling point range of 84.5-98.5oC.
In this experiment, meso-stilbene dibromide was used to produce diphenylacetylene through two sequential dehydrohalogenations. The first part is a concerted E2 mechanism, where the reactant is deprotonated at the beta carbon from the halide ion that will be leaving. This creates a transition state where the leaving hydrogen and halide are anti-periplanar with each other, meaning that they are at a 180° angle in relation to one another. This reaction is caused by a base—in this case, potassium hydroxide—and produces a haloalkene, or vinyl halide. Potassium hydroxide was only added to reaction when needed, as
The purpose of this experiment was to determine the relative reactivities of different types of hydrogen atoms toward bromine atoms. Although the tested compounds were all arenes, their reactivities differ as they contain different types of hydrogens. The hydrogens could be of three different types and could also differ in being bonded to carbons that are attached to a different number of other carbons. The three different types of hydrogens that could be found were aromatic, aliphatic, and benzylic. The first category is aromatic hydrogens, which are attached to sp2 carbons or are those directly bonded to an aromatic ring. Aromatic hydrogens are the least reactive of the hydrogens in this experiment. The second type of hydrogen being investigated is aliphatic hydrogens, which are found bonded to an SP3 hybridized carbon which are bonded to another SP3 hybridized carbon. Aliphatic hydrogens can also be broken down into further categories according to their number of substituents into primary (less reactive), secondary (more reactive), and tertiary (most reactive). The third type of hydrogens are benzylic hydrogens, which are bonded to a SP3 hybridized carbon that is bonded to a benzene ring. Benzylic hydrogens are also broken into primary and secondary categories according to their substituents, and are all more reactive than aliphatic and aromatic hydrogens.
As for the reaction itself, the formation of the radical follows the 3 step process of Initiation, Propagation, and Termination. The short run down of this is that the initiation step makes the radical via hydrogen abstraction, the propagation step forms products, and the termination ends the reaction and gives stable products. The rate determining step in this reaction is in the hydrogen abstraction. During hydrogen
Since the purpose of our experiment was to synthesize Tetraphenylcyclopentadienone from benzyl,dibenzyl ketone,absolute ethanol ,and potassium hydroxyde, we finally got our product at the end which mean we were able to accomplish our purpose. that product is very dangerous for human and very toxics for aquatic organisms.
A unimolecular nucleophilic substitution reaction (SN1) was performed to produce 2-chloro-2-methylbutane from 2-methyl-2-butanol and the reaction yield was 2.15g (20.12mmol, 22.04%). The reaction product was relatively pure because it was determined to be 2-chloro-2-methylbutane from the analysis of infrared (IR) and nuclear magnetic resonance (NMR) spectroscopies. Then, a unimolecular elimination reaction (E1) was performed to produce cyclohexene from cyclohexanol and the reaction yield was 0.762g crude cyclohexene and 0.64g regular cyclohexene (9.28 mmol crude cyclohexene and 7.73mmol regular cyclohexene, 49.2% crude cyclohexene and 41.0% regular cyclohexene). The reaction product was relatively pure because it was determined to be cyclohexene
In order to complete a certain experiment 20g of cyclohexanol was needed to proceed. However, the stock of cyclohexanol in the storeroom was depleted and the compound was on backorder. In order to proceed with the research as quickly as possible, it was decided that the needed cyclohexanol was to be synthesized in the lab.
In this experiment, an electrophilic aromatic substitution reaction was performed through the addition of a nitro group to bromobenzene. The experiment uses the nitronium ion, NO2+, which acts as an electrophile to replace a hydrogen atom in the aromatic system of bromobenzene. The bromine substituent on the benzene introduces the possibility of isomers from the reaction with the nitronium ion: NO2+ can be positioned in the ortho position (making 1-bromo-2-nitrobenzene), the meta position (making 1-bromo-3-nitrobenzene), or the para position (making 1-bromo-4-nitrobenzene). There is also a chance that poly-nitration can occur to produce dinitrobenzene. Since nitro groups are deactivators, it requires high temperatures to add another nitro group to the benzene ring.
F is the least reactive because taking off one of the primary alipathic hydrogens would create a very unstable primary carbon radical. Second would be D because taking off the secondary alipathic would create a slightly more stable secondary carbon radical. The third would E which creates a tertiary carbon radical when taking off the tertiary hydrogen. The fourth would then be A which would create a fairly primary benzyl carbon radical when taking off the primary benzylic hydrogen. The fifth would then be B because taking off a secondary bensylic hydrogen would create a stable secondary benzylic radical. The fastest is then C because reaction the tertiary benzylic hydrogen would create a very stable tertiary benzylic carbon
The experimental value of the maximum wavelength for 1-1’-diethyl-2-2’-cyanine iodide was 525nm and the calculated value when p=0nm is 141nm, which shows that 0nm is too small. To get a penetration distance for the dye Equation 4 was used and the value was 0.2439nm. This value of p is much larger than the original guess made for the penetration distance is the pre-lab. Using the calculated penetration distance from this dye, the wavelength of pinacyanol chloride is calculated to be 654nm. This value is about 50nm off the experimental value, which at this scale is significance. A penetration distance was found for pinacyanol chloride, using its experimental maximum wavelength, giving a value of 0.207nm. Using this value to solve for the
If air is admitted to the sample, that spectrum is replaced by one consisting of a quintet of quintets, which we assign, on the basis of the further experiments described below, to the radical anion (1). Two reasonable routes by which the reaction might occur are illustrated in equation A, where the two rings become linked either by the condensation of cyclo- pentadienyl-lithium with cyclopentadienone resulting from the autoxidation of cyclopentadienyl-lithium, or by the coupling of two cyclopentadienyl radicals. The same spectrum is obtained by the autoxidation of the dilithium salt of dihydrofulvalene (2) prepared by Doering and Matzner's method (equation B) ; the pink colour of the suspension of the dianion (2) in tetrahydrofuran changes first to deep green then to violet when the e.s.r. spectrum of the radical anion becomes apparent. Further autoxidation gives the characteristic orange colour of fulvalene? and reaction of this with a sodium mirror and subsequent photolysis restores the colour and the e.s.r. spectrum of the radical anion. Similarly, electrolytic reduction of the fulvalene shows the same 25- line spectrum(equation
From the observations table, chloride is prominently the most reactive out of the three elements due to the facts a colour change occurred when the aqueous solution of chlorine was mixed with bromine and iodine, exhibiting a more reactive element displacing a less reactive element. In the aqueous solution of bromine, a colour change occurred only when mixed with iodine, justifying the fact that bromine is less reactive than chlorine though more reactive than iodine. Therefore, iodine is the least reactive due to the inability of displacing chlorine or bromine when mixed together, no colour change was evident in any of the
For this experiment, nucleophilic substitution was first observed. The 2-methyl-2-butanol was converted into 2-chloro-2-methylbutane by using an SN1 reaction. The alcohol on the 2-methyl-2-butanol was a tertiary alcohol. To form a good leaving group since the hydroxide ion is a bad leaving group, the tertiary alcohol was protonated with HCl, but since it consists of a fully substituted carbon atom from the carbon oxygen bond, an SN2 displacement cannot occur. Therefore, water is the leaving group that disassociates and leaves a relatively stable tertiary carbocation behind.
Background information: Four categories of contaminants have been identified by environmental scientists and have said to be existent in municipal water supplies. These pathogens can cause disease that can lead to cancer and acute poisoning. Public health officials have taken note of the issue and are now attempting to take action to counter the hazard.