Radical Chlorination of 1-Chlorobutane Stella Greathouse March 3, 2023 Abstract A light-initiated reaction between sodium hypochlorite and hydrochloric acid was done to carry out the radical chlorination of 1-chlorobutane. The product was then extracted using sodium bicarbonate and dried using anhydrous sodium sulfate. The amount of each dichlorobutane product was then found through gas chromatography analysis. These amounts then helped to determine the relative reactivities of the hydrogens in the products and the effect of the chloro-substituent on the relative rate of hydrogen abstraction, which is the rate determining step. Overall, this report will present the data for the radical chlorination of 1-chloro butane and explain why 1,4-dichlorobutane …show more content…
The relative reactivity was found by setting the reactivity per hydrogen of 1,4-dichlorobutane to 1.0. As shown in Figure 4, 1,3 dichlorobutane had the highest yield of 48% and the highest relative reactivity of 3. This is because it replaced the C-H bond that was furthest from the chloro substituent and formed a stable secondary intermediate. Next, 1,4-dichlorobutane had the second highest yield of 24%, but the third lowest reactivity of 1.0. Even though it was the furthest C-H bond from the chloro substituent, it formed a less stable primary radical intermediate. This caused it to have a lower reactivity. However, the farther distance from the chloro substituent and the greater number of hydrogens it could replace during hydrogen abstraction (3 from the methyl group), caused it to have the second highest yield. The third highest yield of 22% and the second highest reactivity of 1.4 was 1,2-dichlorobutane. 1,2-dichlorobutane had a smaller yield because it was closer to the chloro substituent. However, since it formed a secondary radical intermediate, it had a higher reactivity. 1,1-dichlorobutane had the smallest yield of 5.5% and the smallest reactivity of 0.38. Even though it formed a stable secondary radical intermediate, it was directly attached to the chloro substituent. Altogether, the data showed two trends: more stable radical intermediates and a greater distance from the chloro substituent increase the relative yield and relative
This is the result because The iodide displaces the chlorine forming 1-iodobutane. Since iodine is a much better leaving group than chlorine, 1-iodobutane will allow the cyanide ion to displace the leaving group much easier. The sodium ions will then ionically bond with the iodide ions to reform sodium iodide. This process lowers the total activation energy for the reaction. What would be the major product if 1,4-dibromo-4-methylpentane was allowed to react with one equivalent of NaI in Acetone?
The most common atom to be replaced is a hydrogen atom, but occasionally other atoms may also be swapped out by an electrophile. Within this reaction, the substituents connected to the benzene ring demonstrate directing behavior that can affect the formation of the product. These substituents can either act as an ortho/para or meta director, which ultimately determine where the electrophile is added onto the ring. Figure 2. Bromine Production via Potassium Bromate and Hydrobromic Acid.1
Introduction:- In organic chemistry the substitution reactions is the most important reactions, especially Nucleophilic aromatic substitution reactions where nucleophile attacks positive charge or partially positive charge As it does so, it replaces a weaker nucleophile which then becomes a leaving group. The remaining positive or partially positive atom becomes an electrophile. The general form of the reaction is: Nuc: + R-LG → R-Nuc + LG: The electron pair (:) from the nucleophile (Nuc :) attacks the substrate (R-LG) forming a new covalent bond Nuc-R-LG.
This is because B is an intermediate, meaning it is produced and then used. One way in which this rate expression can be written is d[B]/dt. This represents the rate of formation of B, seeing as how the expression is positive, indicating that the amount of B is increasing. The differential rate expression can also be written as –d[B]/dt, representing the rate of consumption of B seeing as how the negative sign indicates a decrease in the amount of B. Lastly, C’s differential rate expression can be written as d[C]/dt= k2[B], the positive value of the expression suggesting that the amount of C is increasing. The reaction ABC is slightly different in experiment one and
In the presence of a nucleophile and good leaving group, an organic reactant in specific conditions is likely to undergo a chemical reaction, namely, nucleophilic substitution. Nucleophilic substitution consists of two different mechanisms, SN1 and SN2. In this experiment, SN2 is the mechanism tested. SN2 is a relatively fast, one-step mechanism in which the nucleophile attacks the organic reactant and the leaving group diverges from the reactant to become a weak base (Fig. 1). The overall speed of the reaction can increase based on the size or basicity of the nucleophile, or the bulkiness of the carbon group with the leaving group.
The Characteristics of Freidel-Crafts reactions in the synthesis of bexarotene Lily C. Draga March 12 2023 Miami University Abstract The purpose of this experiment was to learn about Friedel-Crafts alkylations, acylations, and to perform the second step in the synthesis of bexarotene. The final, purified product had a percent yield of 22.44% and a Rfvalue of .69 which matched the provided standard. Peaks in the IR spectrum like the peak at 3018 cm-1 and another peak at 1384 cm-1represented groups known to be on the desired product. It can be drawn from this research that product 3 (1,1,4,4,6-Pentamethyl-1,2,3,4-tetrahydronaphthalene) was successfully synthesized from this reaction.
Unimolecular - rate depends on concentration of only the substrate. Does NOT occur with primary alkyl halides (leaving groups). Strong acid can promote loss of OH as H2O or OR as HOR if tertiary or conjugated carbocation can be synthesized.15 Comparison of Enolization and Nucleophilic Reactions Enolization Nucleophilic Reactions 1) In this type of reaction tautomerism happens.
The next part of the experiment, alkyl halide classification tests, will be used to determine the degree of substitution of the alkyl halide that was formed during the reaction. For this experiment specifically, this allows for the verification of the formation of a primary bromoalkane from the primary alcohol. The success of the experiment will be determined by a percent yield, analysis of the infrared spectroscopy reading, and the results of the alkyl
Wilfrid Laurier University, ON, Canada. Observation Results: Table 1: Qualitative Observations of all reactants and products in experiment Reactant/ Product Before During
This lab demonstrates the concept of limiting reactants because the amount of product that can be produced is limited by the amount of reactant that is present in the smallest amount. The reactant that is completely consumed is the limiting reactant, and the amount of product that can be produced is determined by the amount of limiting reactant present. In this reaction, HCl was added in excess and NaHCO3 was the limiting
Cholesterol is a steroid alcohol that is constituted as a nonsaponifiable lipid. All steroids play an important role in the secretion of blood in which is vital for the human body to function properly. The carbon-carbon double bond in cholesterol makes the molecule as a whole immensely more reactive than other alkanes. Cholesterol’s ability to be reactive allows it to be capable of undergoing addition reactions because the pi bond electrons can easily bond to other atoms. The addition of a halogen, in this experiment, bromine, creates a vicinal dibromide.
Introduction Purpose The main purpose of this experiment is to learn the principles of stoichiometry. It will help us understand the process of finding moles of each reactant, limiting reagents, and calculating theoretical and percent yields for each reaction. Theoretical Background The stoichiometry depends on the balancing chemical formulas which must have the correct ratios for each reactant, so they can form product properly.
3.1. Optimization of the reaction conditions The experimental parameters affecting the development and stability of the reaction product between the drug and the reagent were investigated and optimized. Each parameter was changed individually while the others were kept constant. These parameters include; pH, buffer (type & volume), concentration of NBD-Cl, reaction and stability time, temperature, acidification and diluting solvent.
Many other chlorinated and brominated aromatic compounds such as tryptophan, tyrosine and many other derivatives of pyrrole are also present in nature. Reactions of haloarenes or reactions of aryl halides can be primarily divided into three types: Nucleophilic Substitution Reactions Electrophilic Substitution Reactions Reaction with Metals The reaction of Haloarenes – Nucleophilic Substitution Reactions
The reaction adds two electrons to the contaminating molecule, thus reducing the contaminant. In order for the reductive dehalogenation to proceed, a substance other than the halogenated contaminant must be present to serve as an electron donor. Possible electron donors are hydrogen and organic compounds of low molecular weight (lactate, acetate, methanol or