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Lecture26-notes - Elimination Reaction In an elimination...

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10/27/09 1 Elimination Reaction In an elimination reaction the starting material loses the elements of a small molecule such as HCl or HBr during the course of the reaction to form the product. Example Alkyl halide + strong base and heat LOSS OF HCl
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10/27/09 2 Elimination In this case the nucleophile reacts as a base; we observe elimination reactions. A hydrogen is removed from a carbon atom. The halogen is removed from the adjacent carbon. Note that the elimination reaction is the reverse of an addition reaction. E2 Reaction The functional group is attached to the α -carbon. α -carbon β -carbon The β -hydrogen is attached to the β -carbon. Since the β -hydrogen is lost this reaction is called a β -elimination.
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10/27/09 3 Mechanism of E2 THE BASE TAKES THE β -HYDROGEN C C C l H B: C C C l H B : : .. : : .. .. Bond formation ( π bond) and breaking bonds (C-H and C-X σ bond ) take place simultaneously Regioselectivity WHAT HAPPENS IF THERE IS MORE THAN ONE β -HYDROGEN? β β α
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10/27/09 4 Regioselectivity β β
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