Essay on Reaction Iodoethane with Saccharin, an Ambident Nucleophile

Ethyl ethanoate is made from ethanol and ethanoic acid. In the reaction sulphuric acid is added as a catalyst.

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 aspirin crystals were washed by pouring 10 mL of water over them through the funnel.

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.

The crude product was washed by taking the reaction product in the separatory funnel and adding 23 mL of deionized H2O. The mixture was shaken and allowed to settle until layers were observable. The top layer was the desired product and approximately 25 mL of aqueous layer was extracted from the separatory funnel. Next, 25 mL of 5% NaHCO3 was added to the separatory funnel in order to neutralize the acid. This mixture was swirled, plugged with the stopper and inverted. Built-up gas was released by turning the stopcock to its opened and closed positions, releasing CO2 by-product. This was done four times in one minute intervals. The solution was allowed to settle until layers were observable. The bottom layer that contained salt, base and water was extracted from the separatory funnel. The crude product was washed again as mentioned previously.

7. Plan: Each student in a group of three will work to purify the product of the reaction with cis-stilbene, trans-stilbene, or styrene. The crude products will be purified through recrystallization. This purification process will be performed several times. When the recrystallization is complete, a vacuum filtration will be executed to filter out the crystals. An NMR spectrum will be taken of the recrystallized product.

The solvolysis of t-butyl bromide is an SN1 reaction, or a first order nucleophilic substitution reaction. An SN1 reaction involves a nucleophilic attack on an electrophilic substrate. The reaction is SN1 because there is steric obstruction on the electrophile, bromine is a good leaving group due to its large size and low electronegativity, a stable tertiary carbocation is formed, and a weak nucleophile is formed. Since a strong acid, HBr, is formed as a byproduct of this reaction, SN1 dominates over E1. The first step in an SN1 reaction is the formation of a highly reactive carbocation, in which a leaving group is ejected. The ionization to form a carbocation is the rate limiting step of an SN1 reaction, as it is highly endothermic and has a large activation energy. The subsequent nucleophilic attack by solvent and deprotonation is fast and does not contribute to the rate law for the reaction. The Hammond Postulate predicts that the transition state for any process is most similar to the higher energy species, and is more affected by changes to the free energy of the higher energy species. Thus, the reaction rate for the solvolysis of t-butyl bromide is unimolecular and entirely dependent on the initial concentration of t-butyl bromide.

The solution that was performed in this experiment was to use sulfuric acid in order to form a protonated alcohol, so when the halogen or nucleophile back attacks the compound, water is displaced. Once the alcohol is protonated, the solution reacts in either an SN1 or SN2 mechanism.

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.

SN1 reactions are considered unimolecular nucleophilic substitution mechanisms and are a first-order process. Meaning that the reaction forms a carbocation intermediate and that the concentration of the nucleophile does not play a role in the rate-determining step, which is the slowest step in the reaction. All of the SN1 reaction mechanisms in this procedure can react two different ways. The expected mechanism for these reactions would be that the carbocation would react with the weak nucleophile nitrate, attaching the nitrogen to the positively charged carbon. However, while nitrate is the intended nucleophile in all of the reactions, it is a poor nucleophile. The ethanol used in this reaction is a polar protic ionizing solvent,

Many reactions that exist in nature involve a double displacement between ions and reactants with solvents. A bimolecular nucleophilic substitution, or SN2 reaction, involves a nucleophilic attack on a substrate and the departure of a leaving group. A nucleophile is a compound or ion that donates electrons to promote bond formation (Caldwell, 1984). In order for a leaving group in a compound to leave, it must possess the characteristics of a weak base and be able to occupy electrons. Several factors affect the rate and favorability of such reaction, such as (Bateman, 1940). In addition, the substrate that is attacked by the nucleophile is commonly an unhindered primary substrate to allow the reaction to occur quicker. An SN2 reaction follows the second-order rate law.

However, the rate of reaction only increases for a certain period of time until there is lesser substrate molecules than the enzyme molecules. The increase of enzyme concentration does not have effect if there are lesser substrate molecules than enzyme molecules initially.

The reaction took place in a conical vial and .2mL of each of the reactant samples were added to it along with some 95% ethanol. Two drops of NaOH were added shortly after and stirred at room temperature for fifteen minutes. The vial was cooled in and ice bath and crystallized. Vacuum filtration was performed to filter the crude product. The crude product was recrystallized using methanol and filtered again. We made one change to the procedure and instead of using .7mL of ethanol we

One of the topics we discussed during lecture was the topic of nucleophiles. This seemed to be a beneficial topic to choose to expand my knowledge upon since nucleophiles are used so often in reactions. So to in order to expand my knowledge on the subject, I chose to research the journal “Ring-Opening Reactions of the N‑4-Nosyl Hough−Richardson Aziridine with Nitrogen Nucleophiles,” by Tomáš Ručil, Zdeněk Trávníček, and Petr Cankař. In their journal, Ručil, Trávníček and Cankař discuss how they synthesized the ring-opening reactions of N-4-nosyl Hough−Richardson aziridine with nitrogen nucleophiles. Then they further expanded on this idea by showing the major and minor products produced by adding nitrogen nucleophiles with Dinosylated