Preview

Reaction Iodoethane with Saccharin, an Ambident Nucleophile

Better Essays
Open Document
Open Document
1080 Words
Grammar
Grammar
Plagiarism
Plagiarism
Writing
Writing
Score
Score
Reaction Iodoethane with Saccharin, an Ambident Nucleophile
Discussion: 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


References: CRC Handbook of Chemistry and Physics, 87th Ed, 2006-2007 Experiment 8 Saccharin Hunt, Ian. “Chapter 8: Nucleophilic Substitution” Department of Chemistry, University of Calgary. March 8, 2009. Lehman, John W Merck Index. V13.1. Merck: Whitehouse Station, NJ. 2001 Richard.”N-Ethylsaccharin” March 8, 2009 Saccharin. Wikipedia. March 8, 2009. http://en.wikipedia.org/wiki/saccharin.

You May Also Find These Documents Helpful

  • Powerful Essays

    Sodium saccharin (0.446 g) was dissolved in N-N-dimethylformamide (DMF) at 80oC. Iodoethane (0.16 mL) was added and heated at constant temperature (80oC) for ten minutes. The product was separated by adding water to the room temperature solution, further cooled in ice and the solid collected and dried via vacuum filtration. The following week, the dried product (0.442g) was analyzed by melting point (87.8-94.7oC), and a 1H NMR spectrum.…

    • 954 Words
    • 4 Pages
    Powerful Essays
  • Powerful Essays

    References: (3) McMurry, J. Organic Chemistry, 5th ed., Brooks/Cole Publishing Co.: CA, 2000, p. 564-566.…

    • 3241 Words
    • 13 Pages
    Powerful Essays
  • Powerful Essays

    Ely Mine

    • 1764 Words
    • 14 Pages

    Seager, S. L., & Slabaugh, M. R. (2000). Chemistry for Today (4th Ed.). Pacific Grove, CA: Brooks/Cole.…

    • 1764 Words
    • 14 Pages
    Powerful Essays
  • Good Essays

    Sn2 Reaction Lab Report

    • 442 Words
    • 2 Pages

    Sn1 Mechanisms the leaving group must be a weak base. The carbon group is part of the rate determining step. The reaction goes faster when the there are stable carbonations. The solvent favors one towards a polar protic…

    • 442 Words
    • 2 Pages
    Good Essays
  • Good Essays

    J. Olmstead, G. Williams, R.C. Burk; Chemistry, Canadian Edition.; John Wiley & Sons Canada, Ltd: Mississauga, Ontario , 2010; pp 72-79.…

    • 1933 Words
    • 8 Pages
    Good Essays
  • Satisfactory Essays

    References: Brown, Theodore; Chemistry: The Central Science, Prentice Hall: Upper Saddle River, New Jersey, 2012…

    • 522 Words
    • 3 Pages
    Satisfactory Essays
  • Better Essays

    Lab Report Chemistry

    • 1396 Words
    • 6 Pages

    The activation energy obtained in Part C, 138.6 kJ/mol is not too far below the theoretical activation energy of 148.526 kJ/mol[6], while Part A confirms the theory that k is dependent on the initial concentration of reactants, since it is a first order reaction. This is clearly depicted in Figure 3, where the alteration of the amount of t-butyl chloride being added to the reaction vessel clearly produced a different rate constant. The findings from Part B of the experiment proved that the reaction followed the SN1 mechanism, with the increased concentration of water in the water/acetone mixture causing the reaction rate to increase due to the usage of polar solvents to stabilize the carbocation being produced during this mechanism in the slow, rate-determining step [5]. However, there were errors in the experiment, which led to the results being slightly off from theory, such as the lower than expected value for the activation…

    • 1396 Words
    • 6 Pages
    Better Essays
  • Powerful Essays

    3 Darrell D. Ebbing , Steven D. Gammon, General Chemistry, 9th ed., Houghton Mifflin, Boston, 2009, p. 426.…

    • 1572 Words
    • 7 Pages
    Powerful Essays
  • Good Essays

    Chem 6c Midterm 1

    • 1631 Words
    • 7 Pages

    All work must be shown on the exam for partial credit. Points will be taken off for…

    • 1631 Words
    • 7 Pages
    Good Essays
  • Good Essays

    References: Zumdahl, Steven S., and Susan A. Zumdahl. Chemistry. 7th ed. Boston: Houghton Mifflin, 2007. Print.…

    • 551 Words
    • 3 Pages
    Good Essays
  • Good Essays

    The first part of this experiment involves the neutralization of strong electrolytes. 40 mL of 2.0 M HCL was used to neutralized 50 mL of 2.0 M NaOH. Both the solutions were mixed in the calorimeter and the temperature was recorded after 2 seconds until it reaches maximum, then every 10 seconds for one minutes, and finally every 30 seconds…

    • 2522 Words
    • 11 Pages
    Good Essays
  • Better Essays

    Nucleophilic Substitution

    • 1771 Words
    • 8 Pages

    The purpose of this lab is to investigate how different factors affect the rate of SN1 and SN2 reactions. SN2 reactions proceed via a one step mechanism in which the incoming nucleophile attacks the electrophilic carbon center from the opposite side of the leaving group. This reaction mechanism implies that the stereochemistry of a chiral center will be inverted. SN1 reactions proceed via two steps, slow dissociation of the C-X bonds to form an intermediate carbocation and a fast second step in which the C-Nucleophile bond is formed. Since the intermediate carbocation is trigonal planar, the nucleophile can attack with equal probability from above or below. This will result in racemization, partial conversion of one enantiomer, of a chiral center, since equal amounts of each enantiomer will result. Substitution reactions are an important class of reactions because of their synthetic utility and importance in understanding the mechanism of a variety of organic reactions.…

    • 1771 Words
    • 8 Pages
    Better Essays
  • Good Essays

    Syllabus

    • 1537 Words
    • 6 Pages

    Prerequisite: Credit for Chem 101 or Chem 103 taken at Fisher, or transfer credit for the first semester of general chemistry lecture, or concurrent registration in Chem 103.…

    • 1537 Words
    • 6 Pages
    Good Essays
  • Better Essays

    [4] C.W. Garland, J.W. Nibler, and D.P. Shoemaker; _Experiments in Physical Chemistry_, 7th ed; McGraw-Hill: Kent Peterson, New York, 2003; p. 104-106, 112-116…

    • 4068 Words
    • 32 Pages
    Better Essays
  • Good Essays

    References: “Techniques in Organic Chemistry”, J. R. Mohrig, C. N. Hammond, P. F. Schatz, W.…

    • 721 Words
    • 3 Pages
    Good Essays