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Solvent effects: Any property of a solvent system that can ... Common Ion (Mass Law) Effect. Special Salt Effect. Factors that influence carbocation formation ...
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Carbocations rearrange. Reaction of benzene with n-propyl chloride and AlCl3 produces isopropylbenzene. The alkylbenzene product is more reactive than benzene, so ...
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Then consider the relative migratory aptitude of the groups that will undergo 1,2-shift. Migratory aptitude aryl alkyl usually H alkyl ...
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Carbocation Analogues: Nitrenium ions? Evidence to ... Evidence against a concerted pathway. A plausible explanation involving the intermediacy of Oxenium ions ...
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Structure, Bonding, and Stability of Carbocations Figure 4.8 Structure of methyl cation. Carbon is sp2 hybridized. All four atoms lie in same plane.
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Alkenes: Electrophilic addition and carbocation rearrangement (McM 6.12) ... Polymerization of alkenes (McM 7.10) Radical polymerization. Cationic polymerization ...
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Experimetal evidence for charge delocalization onto Co2(CO)6 moiety: ... remote propargylic moiety. Syn form (benzyloxy and phenyl) = most ...
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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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2. Relative stability and rearrangements of carbocations ... a. Two-step substitution. b. Unsymmetrical stabilization of a carbocation ...
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EAS in Naphthalene When attack is at C-1, carbocation is stabilized by allylic resonance and benzenoid character of other ring is maintained.
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Carbocations are electrophiles (electron-seekers) ... electrophile (Lewis acid) Fig. 4.11 Combination of tert-butyl cation and ...
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Electrophilic Addition of Hydrogen Halides to Alkenes Electrophilic addition of hydrogen halides to alkenes proceeds by rate-determining formation of a carbocation ...
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3-Bromo-1-butene is formed faster than. 1-bromo-2-butene because allylic carbocations ... 1-Bromo-2-butene is more stable than. 3-bromo-1-butene because it has a ...
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Chapter 20 Bromination/Debromination of Cholesterol Purpose This reaction involves nucleophilic attack by the alkene on bromine, forming a tertiary carbocation with ...
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Y. H. Y. d d. 12.1. Representative Electrophilic Aromatic Substitution ... Rearrangements in Friedel-Crafts Alkylation. Carbocations are intermediates. ...
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... G may stabilize the carbocation intermediate and therefore speed the reaction, or it may raise the energy of the carbocation and slow the reaction.
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for acetal formation from ketones. Important exception: ... Second stage is hemiacetal-to-acetal conversion. involves carbocation chemistry ...
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... Carbon Species carbanion radical carbene carbocation 1. Stabilize ... Carbon Chirality Centers Note that chirality is a property of the ...
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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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More substituted carbocations have more possible hyperconjugation interactions. vacant p-orbital 4.11: Effect of Alcohol Structure on Reaction Rate.
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Markovnikov's Rule In an addition reaction the more ... Summary of H-X Addtion Reactions. nucleophile. electrophile. or. more stable carbocation. 3 2 ...
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Friedel Crafts Alkylation ... Friedel Crafts Alkylation. Reactions of alkyl halide with Lewis acid produces a carbocation. ...
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Reaction Orientation (ortho/meta/para) Examine mechanism of the substitution reaction. For benzene + Br2 : Intermediate: in the delocalized carbocation intermediate,
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... Lone Pair on Bromine Stabalizes Carbocation and Forms Cyclic Bromonium Ion Step 2; Bromide Ion Must Attack from Oppositte Side of Cyclic Bromonium Ion ...
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Alkenes react with many electrophiles to give useful products by addition (often ... More stable carbocation is consistent with steric preferences. 18 ...
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Boron is more stable being bonded to oxygen. Hydration. Addition Reactions. no carbocations are formed in hydroboration reactions, hence no hydride (or alkyl) shifts ...
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... hydration of 1-butene * Achiral Intermediate Gives Racemic Product Addition via carbocation Top and bottom are ... The property is commonly called ...
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The addition of H2 to a double bond leads to the saturated alkane ... Vinal cations are significantly less stable than saturated carbocations ...
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Protonation of double bond yields the most stable carbocation. ... Borane prefers least-substituted carbon due to steric hindrance as well as charge distribution. ...
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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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The remaining sp orbitals form bonds to other atoms at 180 to C-C triple bond. ... Primary vinyl carbocations probably do not form at all ...
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In general the fragmentation proceeds to give mainly the most stable carbocation ... is written to reflect this using brackets ... molecular ion is detected. 14 ...
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carbocation is allylic, but not aromatic. Mechanism of ... RCCl. O. Zn(Hg), HCl. CH2R. permits primary alkyl groups to be attached. to an aromatic ring ...
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Example addition of HBr to 1-butene Achiral Intermediate Gives Racemic Product Addition via carbocation Top and bottom are ... property of a compound that is ...
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Addition of hydrogen bromide to 2-Methyl-propene. H-Br transfers proton to C=C ... Bromide adds to carbocation. Energy Diagram for Electrophilic Addition ...
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If the olefin is not strongly basic, a strong acid is required to generate the carbocation ... Hydride abstraction is a key intermolecular H (hydride) transfer ...
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Dehydration of Alcohols Steps Involved: Convert OH to H2O Loss of H2O and Carbocation formation Removal of H+, resulting in formation of pi bond to complete ...
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Carbon-Silicon bonds does not occurs naturally. ... Stabilization of carbocation at -position. Possibility from donation of C-Si bond to empty p orbital. ...
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(b) R Nu? R-Nu. In the second step the carbocation and the nucleophile. combine. ... R, and the leaving group X?.This is a slow, rate ...
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The electrophile (H ) can add to either C1 or C2. The more stable. product will predominate. ... H (electrophile) formation of more. stable 2o carbocation. When ...
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colorings adjusted to the same scale. 1-propyl cation. CH3-CH2. t-BUTYL CARBOCATION = (CH3)3C ... HO HO !!! LUMO-MAN. CH3-CH2 216.789 kcal / mole. CH3-CH-CH3 ...
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Cl: R. ENERGY PROFILE. SN1 ANIMATION. C. CH3. Ph. Cl: R ... Cl: C. R. CH3. Ph. PLANAR. CARBOCATION. ENERGY PROFILE. C. R. CH3. H. C. R. CH3. Ph. ENERGY PROFILE ...
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Certain carbocations may exist as structures in which the positive charge is ... the vi editor and some commands (e.g., grep) as indicated in the lab handout. ...
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In the 2nd step, this reactive carbocation immediately reacts ... d j vu: Oh no! It is orbitals and electrons again! Electrons are neither particle nor waves. ...
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Alkenes and alkynes The chemistry of unsaturation
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Preparation of Alkyl Halides from Alcohols and Hydrogen Halides ROH + HX RX + H2O Hydrogen halide reactivity HI HBr HCl HF most reactive least ...
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Figure 4.9 Structure of tert-Butyl Cation. Positively charged carbon is ... Consider the three-step mechanism for the reaction of tert-butyl alcohol with HCl. ...
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Substitution and Elimination Reaction of Alkyl Halides By: Ismiyarto, MSi * 4 18 18 9 9 21 21 2 4 6 6 8 11 6 2 6 26 29 32 H C C A B X Y H H H syn-Addition; Metal ...
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Title: Substitution aromatique lectrophile Author: Ed Blackburn Last modified by: eblackbu Created Date: 3/30/1996 4:18:52 PM Document presentation format
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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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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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Mechanism of the Reaction of Alcohols with Hydrogen Halides About mechanisms A mechanism describes how reactants are converted to products. Mechanisms are often ...
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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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Chapter 4 Alcohols and Alkyl Halides
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Conjugation in Alkadienes and Allylic Systems conjugare is a Latin verb meaning
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