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Elimination Reactions

IB Chemistry Power Points Topic 20 Organic Chemistry. www.pedagogics.ca. Elimination Reactions. Elimination of HBr from halogenoalkanes. Recall: nucleophilic substitution of a bromoalkane. Elimination of HBr from halogenoalkanes.

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Elimination Reactions

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  1. IB Chemistry Power Points Topic 20 Organic Chemistry www.pedagogics.ca Elimination Reactions

  2. Elimination of HBr from halogenoalkanes Recall: nucleophilic substitution of a bromoalkane

  3. Elimination of HBr from halogenoalkanes Recall: nucleophilic substitution of a bromoalkane

  4. Elimination of HBr from halogenoalkanes Recall: nucleophilic substitution of a bromoalkane Reaction occurs when bromoethane is added to a dilute NaOH solution. If conditions change, the nature of the reaction will change

  5. Elimination of HBr from halogenoalkanes An elimination reaction is one where a small molecule is removed from the reactant molecule. Substitution OH- + C2H5Br  C2H5OH + Br- Elimination OH- + C2H5Br  C2H4 + H2O + Br- Which reaction occurs depends on the reacting conditions.

  6. Elimination of HBr from halogenoalkanes

  7. Elimination reaction mechanisms • E2 mechanism • - similar to SN2 - bimolecular process • transition state, no intermediates • typical of secondary or tertiary substituted alkyl halides

  8. Elimination reaction mechanisms • E1 mechanism • - similar to SN1 • - unimolecular process • carbocation intermediate • typical of tertiary substituted alkyl halides

  9. Elimination reaction mechanisms How the reactions happen – the role of OH- The hydroxide ion hits one of the hydrogen atoms in the alkyl halide and pulls it off. This leads to a cascade of electron pair movements resulting in the formation of a carbon-carbon double bond, and the loss of the halogen as R-.

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