Preview

Two Reactions: Factors Affecting SN2 Reaction

Better Essays
Open Document
Open Document
1895 Words
Grammar
Grammar
Plagiarism
Plagiarism
Writing
Writing
Score
Score
Two Reactions: Factors Affecting SN2 Reaction
Anthony Young
Partner: Nick Dale
TA: Alekhya
6/15/15
The SN2 Reaction: Factors Affecting SN2 Reaction.
Introduction
In the substitution reactions, the leaving group from the substrate is replaced with the nucleophile. Because of the nucleophile it is called nucleophilic substitution. The lone pair of electrons, present on the nucleophile is used to create a new bond with the carbon atom, from which the leaving group was separated. There are two different mechanisms of nucleophilic substitution: SN1 and SN2. The difference between the two depends on how the reaction occurs.
The SN1 reaction is unimolecular, meaning that the rate of the reaction depends on the concentration of the substrate only. The concentration of the nucleophile does not affect the rate of the reaction. In SN1 reaction, the leaving group leaves first. Forming a carbocation, then nucleophile forms the bond with the positively charged carbon. Therefore the reaction consists of two steps. …show more content…
Since a lot substances can be received a product of an SN2 reaction, the mechanism is widely used.
References
"1-Bromopropane(106-94-5)." MSDS Melting Point Boiling Point Density Storage Transport. N.p., n.d. Web. 14 June. 2015. .
"2-Bromopropane." ChemicalBook---Chemical Search Engine. N.p., n.d. Web. 14 June. 2015. .
"Acetone." ChemicalBook---Chemical Search Engine. N.p., n.d. Web. 14 June. 2015. .
"Diethyl ether." ChemicalBook---Chemical Search Engine. N.p., n.d. Web. 14 June. 2015. .
"Ethyldiisopropylamine." ChemicalBook---Chemical Search Engine. N.p., n.d. Web. 14 June. 2015. .
"Iodoethane." ChemicalBook---Chemical Search Engine. N.p., n.d. Web. 14 June. 2015. .
"Iodomethane CAS#: 74-88-4." Chemical Book. N.p., n.d. Web. 14 June. 2015. .
"TRIPROPYLAMINE (N,N-DIPROPYL-1-PROPANAMINE)." CHEMICALLAND21. N.p., n.d. Web. 14 June. 2015. .
"Triethylamine." ChemicalBook---Chemical Search Engine. N.p., n.d. Web. 14 June. 2015.
Continue Reading
View Writing Issues

You May Also Find These Documents Helpful

  • Powerful Essays

    Heath Chemistry Lab 18A: Factors Affecting Reaction Rate
    • 2334 Words
    • 8 Pages

    Heath Chemistry Lab 18A: Factors Affecting Reaction Rate

    This website was used on October 3, 2014 to help develop a better understanding of collision theory in order to explain the various factors affecting the rate of reaction.…

    • 2334 Words
    • 8 Pages
    Powerful Essays
    Read More
  • Better Essays

    Organic Lab 7
    • 1806 Words
    • 8 Pages

    Organic Lab 7

    “A nucleophile is any neutral or uncharged molecule with an unshared pair of electrons. In the substitution reaction, the nucleophile donates an electron pair to the substrate, leading to the formation of a new bond to the nucleophile, while breaking the existing bond to the leaving group” (Solomons and Fryhle 99-102). The two types of nucleophilic substitution reactions, SN1 and SN2, are identified based on whether the different steps occur simultaneously (SN1) or in two separate steps (SN2). To synthesize the t-butyl chloride, the t-butyl alcohol goes through an SN1 reaction. Also, the nature of the solvent can affect which substitution reaction will occur. Polar protic solvents typically favor SN1 reactions. This is because the SN1 mechanism is carried out in two steps and the polar protic solvent produces both a cation and an anion which are capable of stabilizing the charges on the ions formed during the reaction. Because an SN2 reaction occurs in one step, this is unfavorable; however, the SN2 reactions tend to favor polar aprotic solvents. Another factor affecting the type of substitution reaction is the nature of the leaving group. Since the SN1 reactions occur in one step,…

    • 1806 Words
    • 8 Pages
    Better Essays
    Read More
  • Better Essays

    Reac 714 Studying Sn1 and Sn2 Reactions: Nucleophilic Substitution at Saturated Carbon
    • 1659 Words
    • 7 Pages

    Reac 714 Studying Sn1 and Sn2 Reactions: Nucleophilic Substitution at Saturated Carbon

    References: Jerry Manion. Studying SN1 and SN2 Reactions: Nucleophilic Substitution at Saturated Carbon, Chemical Education Resources, 1998, H.A. Neidig pg 1-16.…

    • 1659 Words
    • 7 Pages
    Better Essays
    Read More
  • Good Essays

    Title: Nucleophillic Substitution Reaction
    • 1152 Words
    • 7 Pages

    Title: Nucleophillic Substitution Reaction

    Introduction: This lab experimented on the reactions of the chemicals that undergoes SN1 or SN2 reaction. Nine different compounds were given to be examined with two reagents - NaI in acetone and AgNO3 in ethanol. The SN1 reaction happens in AgNO3 in ethanol reagents, and SN2 reaction is in NaI in acetone.…

    • 1152 Words
    • 7 Pages
    Good Essays
    Read More
  • Better Essays

    Nitrating Acetanilide and Methyl Benzoate: Electrophilic Aromatic Substitution
    • 3498 Words
    • 14 Pages

    Nitrating Acetanilide and Methyl Benzoate: Electrophilic Aromatic Substitution

    An electrophilic aromatic substitution reaction is the attack of an electrophile on an aromatic ring substituting for a proton. This reaction allows for the introduction of other functional groups onto the aromatic ring. The electrophile attacks the aromatic ring at the aliphatic position removing two electrons destabilizing the aromatic ring, but creating a resonance-stabilized carbocation called a sigma complex (arenium ion). Then the aliphatic proton is lost to give the substitution product.…

    • 3498 Words
    • 14 Pages
    Better Essays
    Read More
  • Good Essays

    Relative Reactivity of Anilines
    • 540 Words
    • 3 Pages

    Relative Reactivity of Anilines

    Results: Through a melting point reading, it was determined that the product obtained was 2,4-Dibromoanisol mp 55-58 C. The products obtained by my partners, were determined to be: (p-bromoacetanilide mp 160-165 C) and (2,4,6 tribromoaniline, mp of 108-110 C) respectively.…

    • 540 Words
    • 3 Pages
    Good Essays
    Read More
  • Satisfactory Essays

    Rxn Of Iodoethane With SodiumSaccharin
    • 747 Words
    • 3 Pages

    Rxn Of Iodoethane With SodiumSaccharin

    The solvent used in this reaction is very important for determining the rate of nucleophilic substitution reaction. Polar protic solvents such as water and ethanol result in bulky solvation shells around the charged nucleophile; this is what reduces its nucleophilic strength. The result is a slower reaction. Polar aprotic solvents do not solvate the nucleophile very strongly, this results in an attack on the substrate. Therefore, polar aprotic solvents accelerate the rates of reaction, especially SN2 reactions, where the strength of the nucleophile determines the rate of reaction.…

    • 747 Words
    • 3 Pages
    Satisfactory Essays
    Read More
  • Satisfactory Essays

    Competing nucleophiles
    • 526 Words
    • 3 Pages

    Competing nucleophiles

    Base on the data table, 1-bromobutane dominated the composition of 85.02%, which indicates the conclusion that the mechanism for 1-butanol is SN2, and bromide is a better nucleophile. The first reason is that the substrate is a primary alcohol. The SN2 reaction is the nucleophilic attack of a central atom which kicks out the leaving group. A primary alcohol only has hydrogens plus the leaving group attached to the central carbon. Since the hydrogens do not hinder the nucleophilic attack, SN2 reaction is favored. The second reason is that bromide is a better nucleophile. Nucleophlicity is an essential factor in SN2 mechanism since the nucleophile is included in the rate determining step.…

    • 526 Words
    • 3 Pages
    Satisfactory Essays
    Read More
  • Satisfactory Essays

    Stereochemistry of Bromine Addition
    • 428 Words
    • 2 Pages

    Stereochemistry of Bromine Addition

    Purpose: To carry out the addition of bromine to trans-cinnamic acid and to identify the product from its melting point.…

    • 428 Words
    • 2 Pages
    Satisfactory Essays
    Read More
  • Good Essays

    How Enzyme Concentration Can Affect Rate of Reaction
    • 857 Words
    • 4 Pages

    How Enzyme Concentration Can Affect Rate of Reaction

    This basically can involve a single molecule or more than one molecule with a complementary shape has a shape that fits into the active site. These molecules which are called substrates form a bond with the amino acids on the active site, to produce an enzyme substrate complex, in this form the substrate molecules react much quicker and easily. The other point to this is each enzyme will only catalyse one specific reaction because only one…

    • 857 Words
    • 4 Pages
    Good Essays
    Read More
  • Good Essays

    Single Replacement Reaction Essay
    • 892 Words
    • 4 Pages

    Single Replacement Reaction Essay

    Chemistry is a branch of science that plays a role in many aspects of life, and one of its goals is to study the interactions caused by the combination of substances. The combination of substances often causes reactions, and one of the main groups of reactions is the single-replacement reaction. In Amrita University’s explanation of single replacement reactions, a single replacement reaction is defined as a “chemical reaction in which a more reactive element displaces a less reactive element from its compound.” The general formula for single displacement reaction is: AB + C  A + BC.…

    • 892 Words
    • 4 Pages
    Good Essays
    Read More
  • Powerful Essays

    Asymmetric Catalylysis Of Α-Diazoketones Lab Report
    • 1560 Words
    • 7 Pages

    Asymmetric Catalylysis Of Α-Diazoketones Lab Report

    Electrophilic addition causes N2 to be lost, which is a thermodynamically favourable process, resulting in the formation of a stable carbene. The carbene is the intermediate and in this reaction, it is a highly reactive, neutral molecule. The carbene acts as an electrophile and proceeds to react with carbon-carbon and carbon–hydrogen bonds. The final step in the process, involves the transfer of the carbene and regeneration of the metal catalyst, hence completing the catalytic cycle.…

    • 1560 Words
    • 7 Pages
    Powerful Essays
    Read More
  • Better Essays

    Reaction Iodoethane with Saccharin, an Ambident Nucleophile
    • 1080 Words
    • 5 Pages

    Reaction Iodoethane with Saccharin, an Ambident Nucleophile

    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
    Read More
  • Satisfactory Essays

    Hydrocarbon
    • 267 Words
    • 2 Pages

    Hydrocarbon

    | * MP&BP * Colourless liquid at RT * Volatile * Soluble in waterDissolve in organic compund * Less dense than water…

    • 267 Words
    • 2 Pages
    Satisfactory Essays
    Read More
  • Satisfactory Essays

    Radical Cations: Generation, Reactivity, and Stability
    • 3008 Words
    • 13 Pages

    Radical Cations: Generation, Reactivity, and Stability

     Secondary reactions play a major role in our generation and use of radical cations.…

    • 3008 Words
    • 13 Pages
    Satisfactory Essays
    Read More