Nucleophilic Substitution Organic Substitution versus Inorganic Single Replacement

Nucleophilic Substitution Organic Substitution versus Inorganic Single Replacement

Nucleophilic Substitution Organic Substitution versus Inorganic Single Replacement Oxidation-reduction, with new ionic bonds, in single replacement Making and breaking covalent bonds in

organic substitution Aromatic and Acyl Substitution Addition/elimination that reconstitutes aromatic system

Addition/elimination that reconstitutes carbonyl group Radical Substitution Nucleophilic Substitution Bimolecular Nucleophilic

Substitution (SN2) Unimolecular Nucleophilic Substitution (SN1) Second Order with Inversion

First Order with Racemization SN2 Inversion versus SN1 Racemization SN2 Inversion SN1 Racemization

Stereospecific Loss of optical purity Kinetics of SN2 versus SN1 SN2

Rate = k[Substrate][Nucleophile] Rate depends on nucleophile conc. Restrictive collision orientation in RDS SN 1 Rate = k[Substrate] Rate independent of nucleophile conc.

Net bond dissociation in RDS Kinetic Control versus Thermodynamic Control Steric Hindrance versus Carbocation Stability

Less hindered substrate favors SN2 More stable carbocation favors SN1 Protic Solvents for SN2 versus SN1 Nucleophile stabilized in SN2

Charged intermediates stabilized in SN1 Protic versus Aprotic Solvents Effect of Nucleophile SN2 could be favored with superior nucleophiles:

Localized, destabilized anion Low electronegativity atom Larger, more polarizable atom

High p-character hybrid orbital Low steric hindrance Factors Favoring SN2 versus SN1 Less hindered substrates favor SN2; substrates with more stable carbocation intermediates favor SN1. Polar aprotic solvents, which avoid sequestration of

nucleophiles, are favored for SN2; protic solvents, which stabilize intermediates, are favored for SN1. Exceptional nucleophiles may improve the preference for SN2 over SN1.

Recently Viewed Presentations

  • TeachWithFergy Preview File

    TeachWithFergy Preview File

    - Luminous and non-luminous objects - History of light - The electromagnetic spectrum - Prisms - Colour . TeachWithFergy Preview File. Please enjoy this preview of your Power Point. Some slides appear blank because they have been removed.
  • Type Title Here

    Type Title Here

    Amendment to the U.S. Lacey Act: Implications for Forest Products Manufacturers, Exporters and Importers Beijing, June 18-19, 2008 R. Juge Gregg
  • Safe Drinking Water Information System: Compliance Monitoring ...

    Safe Drinking Water Information System: Compliance Monitoring ...

    Safe Drinking Water Information System Compliance Monitoring Data & NextGen. Greg Fabian, PMP. to. ... the utilities, and consumers to obtain timely information for learning more about their drinking water and performance of drinking water systems for public health protection...
  • A CASE CHALLENGE IN HFrEF:

    A CASE CHALLENGE IN HFrEF:

    PARADIGM-HF Primary Results: Significant Reduction in Primary Endpoints, CV Death, and All-Cause Mortality
  • Globalization of Norms - Global Freedom of Expression

    Globalization of Norms - Global Freedom of Expression

    Norms "Standard of appropriate behavior for actors with a given identity" - Quality of "oughtness". They must be distinguished from Institutions: collection of practices and . rules. Not all norms are legal norms. Hard and Soft Norms
  • Oral Exams for Actuarial Education - University of Waterloo

    Oral Exams for Actuarial Education - University of Waterloo

    My Experience with Oral Exams. As a grad student, research project and took an oral exam in GordWillmot'sACTSC 966. As an instructor, have given oral exams in: STAT 430/830 (Experimental Design) ACTSC 455/855 (Advanced Life Insurance Practice) ACTSC 613 (Probability...
  • [Title With Capital Letters]

    [Title With Capital Letters]

    Qualificationsrequirements. You must be a full time student. You must have passedlanguagerequirements as stated for each institution. BA MMC. BSc. You must have passedeach of the screening examinations (førsteårsprøver) with a minimum of grade 02
  • Computer Architecture and Data Manipulation

    Computer Architecture and Data Manipulation

    Machine Cycle. Fetch. Decode. Execute. The architecture of the machine described in Appendix C. Start of the Fetch Execute cycle. All of the instructions were fetched and executed as part of the machine cycle. Performing the fetch step of the...