Courtney Copeland
Alexis Madrazo
TA: Katrinah Tirado
October 10, 2017
Synthesis and Reactivity of tert-butyl Chloride via an Sn1 Reaction
Copeland 1
Introduction/Background
Substitution reactions are important chemical processes that contribute to the production of new compounds. Simplistically, these reactions take place through a series of steps in which one functional group is replaced by another (March). There are two types of nucleophilic substitution reactions, first-order and second-order, but this experiment only involves the Sn1 first-order reactions. Sn1 reactions are considered unimolecular meaning that only one molecule is involved in the rate determining step, the slowest step of the reaction which determines the overall speed of the reaction. In contrast, Sn2 reactions are considered bimolecular, and complete the substitution reaction in one step. The main components of these reactions are the nucleophile and the leaving group; a nucleophile replaces the leaving group by donating its electrons to form a new bond to the carbon (Weldegirma). For this experiment, the nucleophiles and leaving groups of the Sn1 reactions are alkyl halides and alcohols respectively. When a hydrogen atom is replaced by halogen in an alkane, the resulting compound is referred to as a alkyl halide. There are certain factors that affect both Sn1 and Sn2 reactions which include the structure of the substrate, and the concentration and reactivity of the nucleophile (Sn2 only). If a
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.
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.
Note that the enzyme remains unchanged so that more of the some substrates can react.
Alkanes are relatively unreactive. There are only a few types of reactions commonly performed. In this lab, halogenation was performed. In the methane molecule, the
Hydrogens, alkyls, or aryls bonded to carboxyl groups—made up of a carbonyl group and a hydroxyl group—are known as carboxylic acids. Derivatives of carboxylic acids include acid chlorides, esters, anhydrides, amides, and generally nitriles. These derivatives are formed by the replacement of the hydroxyl group with a different electronegative heteroatom substituent, which can be a single atom, such as a chlorine atom, or a group of atoms, such as in the formation of
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.
enable the substrate to bind to the enzyme and form the enzyme substrate complex and
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.
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
The purpose of this lab is to understand the process of eliminating an alkyl halide to form an alkene. The experiment is carried out by first converting the alcohol, 2-methy-2-butanol, into the alkyl halide of 2-chloro-2-methylbutane that will then be put through dehydrohalogenation that favors elimination reaction (E2) to create a mixture of 2-methyl-2-butene and 2-methyl-1-butene. A fractional distillation will be taken to purify the mixture and an additional gas chromatography will be done to further analyze the mixture composition. A bromide test will be done to determine the product of an alkene in the experiment.
pathway for the transformation of one to the other. They increase the rates of reactions
Streacker´s Reaction is a term used for a series of chemical reactions that synthesize an amino acid from an aldehyde or ketone. It´s a preparation of α-aminonitriles, which are versatile intermediates for the synthesis of amino acids via hydrolysis of the nitrile.
generally act as a catalase that initially bring about a chemical reaction.” Enzymes play an
Many factors that affect the reaction rate in a system include pressure, temperature, activation energy and concentration. The temperature of a system particularly affects the rate at which a reaction happens. Temperature is a form of kinetic energy and with the addition of energy; more collisions occurs which increases the likelihood that the reactants will exceed the activation barrier. This is similar to the collision theory, as discuss below.