ChemActivity18EliminationReactions - ChemActivity 18:...

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ChemActivity 18: Elimination Reactions Lecture: Organic Chemist’s Periodic Table, Reactants requiring counter ions, and Rates of reactions. Model 1: General Dehydrohalogenation Reaction Alkyl halides undergo elimination reactions with Bronsted-Lowry bases. C C H Cl CH 3 C H 3 CH 3 CH 3 + B : CH 3 CH 3 C H 3 C H 3 + H B + Cl - + : : : CTQs 1) What two elements are removed from the hydrocarbon starting material in Model 1? Hydrogen and chlorine What new structural feature is formed in the hydrocarbon product? alkene 2) Label the carbon connected to the chlorine atom as α , which means “atom immediately adjacent to” 3) Label the next carbon as β . This is the atom next to the α atom. 4) Dehydrohalogenation reactions are also called β elimination reactions . Suggest an explanation for this terminology. You are pulling off the hydrogen on the beta carbon….
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Model 2: E2 Elimination (One Step Dehydrohalogenation Reaction) C C H Cl CH 3 C H 3 H H + C C H H C H 3 C H 3 + O H O H H : : : : + Cl : : One step Rate= k [alkyl halide][base] 5) Label the α and as β carbons. 6) On the model reaction above draw curved arrows to propose a mechanism for the formation of the products. (Hint: Chlorine leaves via backside attack) 7) The halogen is on which of the following types of carbon: primary, secondary, tertiary,
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This note was uploaded on 04/08/2008 for the course HIST 101 taught by Professor Tranel during the Summer '97 term at St. Louis College of Pharmacy.

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ChemActivity18EliminationReactions - ChemActivity 18:...

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