Preview

Sn1 Reactivity Of Tert-Butyl Chloride

Good Essays
Open Document
Open Document
635 Words
Grammar
Grammar
Plagiarism
Plagiarism
Writing
Writing
Score
Score
Sn1 Reactivity Of Tert-Butyl Chloride
In this experiment, the objective is to successfully perform an SN1 reaction to determine the reactivity of tert-butyl chloride, through the usage of sodium iodide/silver nitrate reagents and to synthesize tert-butyl chloride. The tert-butyl chloride was synthesized through the use of separation (aqueous and organic layers) and distillation. Tert-butyl chloride is the alkyl halide which is being synthesized throughout the course of the experiment. Alkyl halides are derived from alkanes. Once an alkane has its original hydrogen atom replaced with a halogen, it is now considered an alkyl halide (UC 2016). This experiment utilizes chlorine as the halogen that takes the place of the hydrogen atom. Alkyl halides are versatile, and with little effort …show more content…
SN1 reactions typically take place over the course of two steps. The first step is the slower of the two steps. It involves the departure of a leaving group, which forms a carbocation as the bond between the carbon and leaving group is ionized. This step can be expedited through the use of polar solvents or alkyl halides. The second step of an SN1 reaction entails the formation of the substituted product by a nucleophile attacking the carbocation (Weldegirma 2016). The SN2 reaction is quicker than SN1 reaction because it is a concerted mechanism. This means that the two parts of the reaction occur simultaneously. The two parts of the reaction include the leaving group getting displaced, and the nucleophile’s attack. In an SN2 reaction, there is something called a backside attack. A backside attack involves the unshared electron pair of the nucleophile, attacking the carbon that bonds to the halogen that will be removed. This attack takes place on the face of the molecule that is opposite to the position of the leaving group (Weldegirma 2016). In SN2 reactions, there are two components involved in the transition phase. This differs from SN1 reactions because SN1 reactions have only one component in the transition phase. Also, SN2 reactions result in the molecule being inverted because of the backside attack (Curtis

You May Also Find These Documents Helpful

  • Satisfactory Essays

    Halide Ions Lab

    • 618 Words
    • 3 Pages

    Purpose: The purpose of this lab is to observe the reactions of halide ions with different reagents by mixing them together. Analyze data to determine characteristic reactions of each halide ion. Infer the identity of unknown solutions.…

    • 618 Words
    • 3 Pages
    Satisfactory Essays
  • Good Essays

    This initial reaction is called the initiation step of the mechanism. Once the high-energy chlorine free radicals are formed, the energy source (UV light or heat) can be removed. The energy liberated in the reaction of the free radicals with other atoms is sufficient to keep the reaction running.…

    • 1325 Words
    • 6 Pages
    Good Essays
  • Good Essays

    Sn1 Lab

    • 759 Words
    • 4 Pages

    An SN1 reaction is a nucleophilic substitution reaction where the rate determining step of the reaction is unimolecular, thus, the rate equation is often shown as having first-order dependence on electrophile and zero-order dependence on nucleophile. This relationship holds for situations where the amount of nucleophile is much greater than that of the carbocation intermediate. The reaction (which involves a carbocation intermediate) is commonly seen in reactions of secondary or tertiary alkyl halides under strongly basic conditions or, under strongly acidic conditions (in this case strongly acidic conditions), with secondary or tertiary alcohols. In this reaction, the alcohol will be protonated by the hydrochloric acid. H2O will then “leave” the molecule in the rate-determining step, forming a relatively stable tertiary carbocation (which is highly substituted). The chloride ion, acting as a Lewis base will donate a pair of electrons to the carbocation (acting as a Lewis acid) forming the…

    • 759 Words
    • 4 Pages
    Good Essays
  • Powerful Essays

    Using SN1 reaction mechanism with hydrochloric acid, t-Pentyl alcohol was converted to t-Pentyl chloride in an acid catalyzed reaction. The reaction took place in a separatory funnel designed to separate immiscible liquids. The crude product was extracted by transferring a solute from one solvent to another. The process of washing the solutions by phase transfer was used in order to remove impurities from the main solvent layer. Finally, the crude product was dried with anhydrous Calcium chloride and purified once more by simple distillation technique.…

    • 1041 Words
    • 5 Pages
    Powerful Essays
  • Better Essays

    In this experiment, we alkylate sodium saccharin to N-ethylsaccharin with iodoethane in an aprotic solvent N,N dimethylformamide. Nucleophiles in this experiment will react better in an aprotic solvent. Aprotic solvents have dipoles due to its polar bonds but they do not have H atoms that can be donated into a H-bond. The anions which are the O- and N- of sodium saccharin are not solvated therefore are “naked” and the reaction is not inhibited and preceded in an accelerated rate. The reaction was an SN2 reaction. Since the Oxygen and Nitrogen are more electronegative than the carbon on which they’re attached electrons are pulled towards O- and N- attracting the ethane from Iodoethane. Iodine being more electronegative breaks off from ethane and joins the Na+. Since, the Oxygen of sodium saccharin is more electronegative than the nitrogen therefore this gives oxygen a higher partial negative charge therefore an attack on Oxygen will give a product that is formed faster; this can be called a kinetic product. The transition state energy is lower than a product formation by thermodynamic control. At thermal equilibrium at 80°C a more stable product is form from a higher transitional state energy. The nucleophiles in the molecule sodium saccharin are O- and N- and the major product formed depending on which oh the nucleophile was attacked most in the reaction. Nucleophilic attack by nitrogen will yield N-ethylsaccharin and nucleophilic attach by oxygen will yield O-ethylsaccharin. “N-saccharin is more stable than O- ethylsaccharin because the Ethyl group is attached to the Nitrogen giving the same spacial configuration for the five membered ring (which is flat or planar).” (Richard y.a.). The carbonyl carbon is sp2 and flat. This has little ring strain and is stable. The first bond between carbon and oxygen in a carbonyl group is created by overlapping an sp2 hybrid orbital from carbon with an sp2 hybrid orbital from oxygen (sigma bond). The second bond…

    • 1080 Words
    • 5 Pages
    Better Essays
  • Better Essays

    Organic Lab 7

    • 1806 Words
    • 8 Pages

    Alkyl halides are compounds in which a halogen atom replaces a hydrogen atom of an alkane. Alkyl halides are classified as primary, secondary or tertiary depending on the number of alkyl substituents directly attached to the carbon attached to the halogen atom. The purpose of this lab was to properly prepare t-butyl chloride from t-butyl-alcohol in a concentrated hydrochloric acid. The reaction occurs through a nucleophilic substitution, which is when a nucleophile replaces the leaving group in the substrate. In this lab, the hydroxyl group of t-butyl alcohol is replaced by a chlorine atom. The reaction proceeds through an SN1 mechanism (Weldegirma 38-41).…

    • 1806 Words
    • 8 Pages
    Better Essays
  • Good Essays

    Introduction: In this lab, we specifically used elimination reaction; however we only used the E1 reaction. In the presence of strong acids, alcohols protonate to form a good leaving group, namely water. Upon loss of a proton to a good leaving group, an introduction of unsaturation (a double bond) can be preformed. According to Wikipedia, an E2 reaction is typically of secondary and tertiary substituted alkyl halides. An E2 reaction results in formation of a Pi bond. The reason we only used an E1 reaction is because the alcohol functional group was attached to a tertiary carbon, which makes it very compatible to have the compound go through an E1 reaction. In addition, we were using sulphuric acid with heat, it is considered as a weak base making the reactivity for an E1 reaction strong. The reaction also would favor a protic solvent in order for it to be an E1 reaction. When the compound goes through the E1 reaction, it forms a carbocation, and in some cases it could be formed on a secondary carbon. This is when you will see rearrangement of hydrogen to put the compound in more stable alkenes. The stability of the carbocation plays an important role in the amount of alkenes formed. In an E2 reaction, we use a compound that is attached to a secondary or primary carbon. The reactivity is better in those conditions and also when heat is used.…

    • 774 Words
    • 4 Pages
    Good Essays
  • Good Essays

    Bromocyclopentane reacts under SN1 and SN2, but it shows a faster reaction in AgNO3/ethanol reagent, that is SN1. This is because bromocyclopentane is secondary bromine, and have bigger steric strain, since it is a cyclic compound. The bigger steric in a molecule, the harder it is for the nucleophile to attack the leaving group (-Br) from the opposite sides, therefore, SN2 reaction is slower than SN1 for bromocyclopentane. From this reaction, precipitation occurs to give out AgBr in ethanol and NaBr in acetone.…

    • 1152 Words
    • 7 Pages
    Good Essays
  • Good Essays

    All In The Family Lab

    • 413 Words
    • 2 Pages

    The purpose of the lab “All in the Family” was to compare the reactivity of the halogens Chlorine, Bromine, and iodine by observing the reactions between their elemental forms and their ionic forms. To accomplish this experiment, we first added a squirt of pet ether to two test tubes. Then, we added the same amount of Cl2 to both of the tubes, shook the mixtures, and recorded the color that resided in each mixture as the initial color. After, a squirt of NaBr was added to one test tube, and a squirt of Nal was added to the other in order to view the reaction between both of the Halides with Cl2. Both test tubes were shaken again, and the colors that remained was noted. The same process was repeated 2 seperate times but instead with Br2 and I2 as…

    • 413 Words
    • 2 Pages
    Good Essays
  • Powerful Essays

    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 shape than 1-butanol. As hypothesised, when 1-butanol and 2-butanol samples were mixed with potassium permanganate in a test tube, signs of oxidation reactions resulted.…

    • 1459 Words
    • 6 Pages
    Powerful Essays
  • Satisfactory Essays

    Exam III: Chemistry 2211

    • 439 Words
    • 2 Pages

    E) Statements (The reaction is fastest with 1° halides), (The reaction follows second order kinetics), and (Changing the identity of the leaving group changes the rate of the reaction) are…

    • 439 Words
    • 2 Pages
    Satisfactory Essays
  • Satisfactory Essays

    Gas Chromatography Lab

    • 648 Words
    • 3 Pages

    E1 reactions are two-step unimolecular reactions. The first step of an E1 reaction occurs when a leaving group, which consists of a weak base, leaves an organic compound, leaving an intermediate carbocation. In the second step, a carbon on the organic compound is deprotonated by a Lewis base, resulting in the formation of an alkene. The dehydration reactions of 1- and 2-Butanol with sulfuric acid occur through an E1 mechanism, so they follow the steps previously…

    • 648 Words
    • 3 Pages
    Satisfactory Essays
  • Better Essays

    Alcohol and Ir Spectrum

    • 1927 Words
    • 8 Pages

    Background: Alcohols are capable of being converted to metal salts, alkyl halides, esters, aldehydes, ketones, and carboxylic acids. In this experiment the conversion from alcohol to alkyl halides was investigated. Alkyl halides are a group of chemical compounds derived from alkanes containing one or more halogens. They are used as flame retardants, refrigerants, propellants, solvents, and pharmaceuticals. As a group, students convert three alcohols to alkyl halides under acidic conditions and record the 13C NMR spectrum in each case. The reaction that takes place in the conversion is a bimolecular nucleophilic substitution, or SN2 reaction. Alcohols do not undergo the same SN2 reactions commonly observed with alkyl halides. There are four aspects that determine the rate of the SN2 reaction: nucleophile, substrate, solvent and the leaving group. This reaction requires a lone pair from a nucleophile to donate an electron-pair in the formation of a chemical bond; it then attacks the bonds to an electrophilic…

    • 1927 Words
    • 8 Pages
    Better Essays
  • Good Essays

    The overall goal of this experiment is to understand and be familiar of SN1 reactivity. We also learned how to prepare 2-Bromobutane by learning how to distill and extract this product from its organic layer. Finally, another goal was to specifically understand the relative reactivity of alkyl halides under SN1 conditions by reacting the alkyl halide and silver nitrate in ethanol.…

    • 762 Words
    • 4 Pages
    Good Essays
  • Good Essays

    Introduction: For this lab, the main focused involved alkanes and hydrocarbons. Essentially, the free-radical chain of chlorination of 1-Chlorobutne. Free radical-chains occur because alkanes are chemically unreactive with most agents. However, the free-radical chain allows a pathway of certain functional groups like alkyl chloride or bromides.…

    • 1378 Words
    • 6 Pages
    Good Essays