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SN1 and SN2 Reactions SN1 SN2 Rate =k[RX] =k[RX][Nuc:-] Carbocation intermediate? Y N Stereochemistry mix Inversion of configuration Rearrangement ~H, ~ CH3 possible
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Substitution and Elimination Competing Reactions SN1 & SN2 vs. E1 and E2 Formation of Alkenes Two Reaction Types Two Reaction Types Elimination versus Substitution ...
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Plotting ln[A]t against t gives a straight line with slope -k: ... Idem, from statistical mechanics (collision theory) ... Idem, from transition state theory: ...
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... polarity causes the carbon to become activated to substitution reactions with nucleophiles. Carbon-halogen bonds get less polar, longer and weaker in going ...
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Potential Energy Diagrams for Multistep Reactions: The SN1 Mechanism Recall... the potential energy diagram for proton transfer from HBr to water Extension The ...
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Chapter 6 Ionic Reactions---Nucleophilic substitution and elimination reactions of alkylhalides (
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Title: PowerPoint Presentation Author: F.P.J.T. Rutjes Last modified by: Rutjes Created Date: 10/4/2000 7:27:45 AM Document presentation format: Diavoorstelling
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Click a box below to go to the mechanism Click here for advice Homolytic Free Radical Substitution Free Radical Addition Heterolytic Electrophilic Addition
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??? ?????? ???? SN1. ???? ???????? ???. ?????? ???????? ... acetone. ???????? ??????. Reaction coordinate. E. ??? ??????. E. E. E E. ??? ???????? ?????? ...
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Title: PowerPoint Presentation Author: Jon A Preece Last modified by: preecjaz Created Date: 1/17/2002 5:43:54 PM Document presentation format: On-screen Show
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tertiary, allylic. or benzylic. H2O. Grignard. Reaction. H3O Mg ... 3o, allylic, benzylic alcohols by SN1. the halide. is often. racemized (acid assisted) ...
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Species with higher electronegativity have tightly held ... Bimolecular or Unimolecular refers to the number of specie(s) involved at the transition state. ...
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Elimination Reactions Consider the following reactions: Are these reactions as simple as this? No. With any substitution reaction we must always consider the ...
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This mechanism is designated SN1 where S = substitution N = nucleophilic 1 = unimolecular (only one species is involved in the rate-determining step) ...
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For SN2, HCCI, CH2=CHI, CH3CH2I, FCH2CH2I. What is CH3CH2I? ... is react compound A with BH3, then alkaline H2O2, next PBr3, and finally cyanide? ...
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An electrophile is a molecule or ion that is attracted to electron-rich regions ... An electrophilic addition reaction is an addition reaction which happens because ...
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nucleophilicity is the affinity of a species ... Steric Hindrance. 30 react with SN1 mechanism, 10 with SN2 and 20 can undergo both ... Steric hindrance for SN2 ...
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6-membered rings - electron deficient - reactive in Nu-fil. Ar subst. 2 / 4 Pos. ... Metal - Halogen Exchange. R-Li: Alkyllithium, NOT LDA etc. ...
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... and aryl halides can all be used to form organolithium and organomagnesium compounds However, these organometallic compounds cannot be prepared from ...
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Chapter 11 Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols Paula Yurkanis Bruice University of California, Santa Barbara Protonating an Amine Does Not ...
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... methyl bromide methanol ethyl acetate acetate and ethanol at ambient pH, reactant and product concs, ...
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Enthalpy Change (DH ) in a Rxn. ... energy contributes to the overall enthalpy of a reaction. ... Enthalpy (DH) of Halogenation Reactions. Energy Diagrams ...
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RBr solvolysis in aqueous formic acid. Alkyl bromide Class Relative rate. CH3Br Methyl 1 ... nucleophile (solvolysis) SN2 mechanism in the presence of a good ...
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There is a strong difference in reactivity between isolated (unconjugated) ... Consider the nucleophilic substitution of an allylic halide via an SN1 mechanism ...
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1. Structure of alkanes - staggered, eclipsed, gauche, Newman diagrams ... cyclohexane - axial versus equatorial, ring flips. mono and disubstituted cyclohexanes ...
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Alcohols and ethers have to be activated before they can undergo a substitution ... Protonation of the amine moiety does not solve the. problem ...
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Organic halides are flammable, and ... Reaction Mechanism SN2 reaction occurs in one smooth step and gives the product with the inverted configuration with ...
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11.1 The Discovery of Nucleophilic Substitution Reactions Walden 11.2 The SN2 Reaction Reaction Kinetics SN2 Process SN2 Transition State 11.3 ...
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The Effects of Temperature and Catalyst on Reaction Rate 15 15.1 Activation Energy and Arrhenius Equation 15.2 Interpretation of Rates of Gaseous
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... functionalization of arenes by diboron reagents catalyzed by iridium complexes: ... electron count for each iridium complex. Oxidative addition of C-C bonds. 6 ...
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The atom or group that is substituted or eliminated in these reactions is called ... Steric hindrance raises the energy of the transition state, slowing the reaction ...
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A compound with an electronegative atom bonded to an sp3 ... Larger than second row anion nucleophile. Weaker base with other substitution-enhancing cond's ...
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Chapter 8: Addition Reactions Addition Reactions to Alkenes (Section 8.1) Markovnikov s Rule (Section 8.2) Stereochemistry of Ionic Addition to Alkenes (Section 8.3)
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Nucleophile weak lewis base (neutral) Strong lewis base, high conc. ... Substitution: preferred with primary halides and polarizable, small. nucleophiles ...
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THIRD version of all the mechanisms Edexcel specify (2002/3) for AS and A2. Mechanisms revealed by left clicking the mouse or using the keyboard a single step at a ...
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PCC can also be used to oxidize 2 alcohols to ketones. Oxidation of 2 Alcohols ... Ethanol oxidizes to acetaldehyde, then acetic acid, a normal metabolite. ...
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Friedel-Crafts alkylation forms a new C-C bond between an aromatic ring and an alkyl group. ... F-C acylations are free of two major limitation of F-C ...
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Characteristics of SN2 Reactions Single Step Mechanism Inversion of configuration SN2 reactions are generally reliable only when the alkyl halide is primary ...
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However, a carbocation forms .! But aren t carbocations UNSTABLE ? ... The negative ion then attacks the carbocation minor How about this reaction .?
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Nucleophilic Substitution Reactions: Competing Nucleophiles. Experiment 21 (4th ed. ... Ex: Acetone & DMSO. Nucleophilic Strength ...
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REACTION MECHANISMS IN ORGANIC CHEMISTRY Imortant Terms: Electrophiles: electron poor reagents, they seek electrons. Nucleophiles: electron rich reagents, they donate ...
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When the solvent is the nucleophile, the process is called solvolysis. ... Dissociation of the C-X bond to form a carbocation intermediate ...
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SN2 is blocked by steric hindrance and back-bonding of extra halogens. ... Both steric and polar effects are important for base-catalyzed hydrolysis. ...
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... a base removes the elements of an acid, HX, from the organic starting material. ... Removal of the elements HX is called dehydrohalogenation. ...
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... Stereoelectronic effect H that is removed by base must be anti periplanar to Br No anti periplanar H atoms in trans stereoisomer; ...
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SN1, SN2, E1, and E2 Flow Chart Dr. Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University SN1, SN2, E1, and E2 Flow Chart Dr. Susan F ...
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Sigma Complex. Intermediate is more stable if nitration occurs ... But halogens have lone pairs of electrons that can stabilize the sigma complex by resonance. ...
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Dallas County Community College District. 2003, Prentice Hall. Organic Chemistry, 5th Edition ... Alcohol as an Electrophile ...
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The ring is deactivated for E-fil ar subst. Less reactive than benzene ... Deactivating, but o/p directing!! Inductively strong. withdrawing effect ...
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Dehydrate with conc. H2SO4, then add H2. Tosylate, then reduce with LiAlH4. Reaction with HBr ... Bimolecular dehydration produces ether. Low temp, 140 C and ...
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What does the transition state of the neuraminidase-catalyzed reaction look like? Homework Questions: Describe the methods used for diagnostic testing for HSV.
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... are treated with sodium iodide in acetone and with ethanolic solution of silver nitrate. In the first case (I-/acetone) the SN2 reaction is favored, while the ...
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Alkenes: Formation by elimination reactions (McM 11.12, 11.13) ... Palladium catalyzed coupling reactions (Lab ex. 10) Met: -ZnX, -B(OH)2, -SnR3 (-MgX) ...
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11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations Based on McMurry s Organic Chemistry, 7th edition * 11.9 Elimination From Cyclohexanes ...
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Chapter 10. 1. Reactions of Alcohols, Ethers, Epoxides, and Sulfur ... Conversion of Alcohols ... Tetrakis(triphenylphosphine)palladium, Pd(Ph3P)4, is a ...
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