Free-Radical Chain Reactions: Bromination of Arenes Post Lab Report Reference: Experimental Organic Chemistry: A Miniscale and Microscale Approach 6th ed., by Gilbert and Martin, Chapter 9 Discussion: The purpose of the experiment as to explore how different hydrogen functional groups in hydrocarbons react with bromine through free-radical chain substitution. The product is dependent on the type of hydrogen that is being subjected to the bromination, whether that be aliphatic, allylic, benzylic, vinylic, acetylenic, or aromatic. By comparing the relative reactivity rates between the different hydrogens to bromine, a hypothesized ranking of reactivity was made of the provided hydrocarbons: toluene, ethyl benzene, tert-butylbenzene, cyclohexane, and methylcyclohexane. This hypothesis was then tested during the actual lab period by preparing two sets of reactions for each hydrocarbon: one in light and one in dark. Observations were noted throughout a thirty minute period in order to determine the experimental order of reactivity. Free-radical chain reactions are one of the few mechanisms that allow for functional …show more content…
Ethylbenzene was predicted to react first due to the secondary benzylic hydrogens present, the most reactive hydrogen for the three main hydrogen functional group classifications. Toluene contains primary benzylic hydrogens, the second most reactive hydrogen. Tert-butylbenzene contains primary aliphatic hydrogens but also an arene ring, allowing for aromatic hydrogens to also be present. This is why it was ranked above methylcyclohexane in the original proposed ranking. Methylcyclohexane contains tertiary, secondary and primary aliphatic hydrogens. Cyclohexane contains just secondary aliphatic hydrogens, justifying its place as the slowest of the hypothesized ranking
The objective of this laboratory experiment is to study both SN1 and SN2 reactions. The first part of the lab focuses on synthesizing 1-bromobutane from 1-butanol by using an SN2 mechanism. The obtained product will then be analyzed using infrared spectroscopy and refractive index. The second part of the lab concentrates on how different factors influence the rate of SN1 reactions. The factors that will be examined are the leaving group, Br versus Cl-; the structure of the alkyl group, 3◦ versus 2◦; and the polarity of the solvent, 40 percent 2-propanol versus 60 percent 2-propanol.
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 Hydroxyl group on alcohols relates to their reactivity. This concept was explored by answering the question “Does each alcohol undergo halogenation and controlled oxidation?” . Using three isomers of butanol; the primary 1-butanol, the secondary 2-butanol and the tertiary 2-methyl-2-propanol, also referred to as T-butanol, two experiments were performed to test the capabilities of the alcohols. When mixed with hydrochloric acid in a glass test tube, the primary alcohol and secondary alcohols were expected to halogenate, however the secondary and tertiary ended up doing so. This may have been because of the orientation of the Hydroxyl group when butanol is in a different
We used TLC analysis to identify each product obtained from the dihydroxylation reactions by spotting a TLC plate with the product of our reaction, a solution of cis-cyclohexane, trans-cyclohexane, and a 50:50 mixture of the two. We then placed the plate in a beaker with ethyl acetate saturating the atmosphere to allow the TLC plate to develop. Finally, we compared Rf values of the components of the mobile phase, after the phase was completed. 100% ethyl acetate was used instead of 100% Hexane or a mixture of Ethyl Acetate, because ethyl acetate has high polarity and can separate the components of a mixture to elution, unlike hexane, which is non-polar, and therefore unable to separate the components of the mixture. A 50:50 mixture of both would not work, because the polar and non-polar compounds would neutralize the mixture, and thereby not separate the components of the mixture.
The purpose of this experiment is to distinguish the relationships between reactants and products, in addition to expanding on concepts such as single displacement reactions, mole ratio values, moles to mass, theoretical yields, limiting reactants, excess, stoichiometric relationships and percentage errors.
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.
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.
Purpose: The purpose of this experiment is to observe a variety of chemical reactions and to identify patterns in the conversion of reactants into products.
~ ~ is the simplest, and most important of the Alkenes. It is one of the most important Petrochemicals
Radicals are further formed in the propagation step, and are combined during the termination step. Since any of the radicals can combine in the termination step, a radical-initiated reaction can produce a mixture of products.3 The purpose of this experiment is to obtain a mixture of isomeric dichlorobutane in order to discover the relative reactivities of 1-chlorobutane through radical initiated chlorination. Instead of heat or light, the initiator used in the experiment is 2,2’-azobis-(2-methylpropionitrile).4 Identification of the products obtained in the experiment was done through the analysis of data from mass spectrometry, gas chromatography, and physical properties (e.g. boiling point and molecular weight).
Alkynes are a functional group that display antibacterial properties as well as antiparasitic and antifungal characteristics1. Due to the presence of the carbon triple bonded carbon that is present in all alkynes, alkyne compounds are crucial in commercial synthesis of compounds due to its ability to undergo multiple chemical reactions such as synthesis to form plastics such as polyethylene.2 Research with alkynes has also lead alkyne containing compounds to be considered possible fuels for rockets as well as welding, for example, an acetylene torch.2 For this specific reaction, trans stilbene undergoes halogenation by acetic acid, opening up the double bond for the PHPB to deposit two bromines which bond to the structure forming the meso stilbene dibromide in the first synthesis step. In the second synthesis step, the meso stilben dibromide undergoes dehydrohalogenation, removing both the Bromine and Hydrogen atoms resulting in the formation of the alkyne group for the compound
During the halogenation reactions of 1-butanol, 2-butanol, and 2-methyl-2-propanol, there is a formation of water from the OH atom of the alcohol, and the H atom from the HCl solution. The OH bond of the alcohol is then substituted with the Cl atom. Therefore all of the degrees of alcohol undergo halogenation reactions, and form alkyl halides as products. This is because the functional group of alkyl halides is a carbon-halogen bond. A common halogen is chlorine, as used in this experiment.
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.
Catalyst loading was varied from 1.91-11.50% (w/w) of the reactants. The conversion of reactant is found to increase with increase in catalyst loading from 1.91% to 11.5% (Figure 7). It is observed that up to the catalyst loading of 7.66% conversion of toluene increases sharply due to the presence of a large number of active sites available for the reactants. However, above catalyst loading of 7.66% although the surface area is provided for reaction, the increase in toluene conversion is negligible due to the shortage of limiting reactant in constant feed flow.
N cis -cyclooctene (61.2 mol%) N indene (47.2 mol%) N cyclododecene (43.4 mol%), totally different from the descending order of the epoxi de selectivity of cyclododecene (100%) N cis -cyclooctene (98.8%) N indene (90.7%) N α -pinene (56.1%). The oxidative by-products of α -pinene include verbenol (13.5%) and verbenone (30.4%), and that of indene is 1-indanone (9.3%). The reactivity of linear terminal 1-decene with air is negligible, because of low π -electron density weakening the ability of electrophilic