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Highlights of Elimination Reaction ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Elimination Reactions ,[object Object],[object Object],[object Object],[object Object]
E1 Reactions  ,[object Object],[object Object],[object Object]
The E1 Reaction The alkyl halide dissociate, forming a carbocation The base removes a proton The mechanism shows that an E1 reaction is a two-step reaction
Alkyl Halides and Elimination Reactions ,[object Object],Mechanisms of Elimination—E1 rate = k[(CH3)3CI] ,[object Object],[object Object]
E1 Mechanism ,[object Object],[object Object],Nucleophile -> acting as a strong base
Energy Diagram for E1
Transition States Rate =  k [A] See SN1 and E1 Reaction Mechanisms And Radical Chain  Reaction
 
Here are four characteristics that the  E1 / SN1 mechanisms have in common.
Dehydration of Alcohols Acid assisted reactions are always E1
The E2 Mechanism
Energy Diagram for the E2 Mechanism
Transition States Rate =  k [A][B] See SN2 and E2 Reaction Mechanisms
 
Alkyl Halides and Elimination Reactions ,[object Object],[object Object],Mechanisms of Elimination—E2 rate = k[(CH3)3CBr][ ¯ OH] ,[object Object]
[object Object],[object Object],[object Object],Alkyl Halides and Elimination Reactions Stereochemistry of the E2 Reaction:
Here are four characteristics that the E2 / SN2  mechanisms have in common.
Effect of the Substrate on E2 Reactivity
Bulky leaving groups: Hofmann Elimination This give the  anti-Saytzeff  product (least substituted product is formed)!
Orientation of elimination: regiochemistry/ Hofmann’s Rule ,[object Object],Less branched More branched
Alkyl Halides and Elimination Reactions ,[object Object],General Features of Elimination
Alkyl Halides and Elimination Reactions ,[object Object],General Features of Elimination
Alkyl Halides and Elimination Reactions ,[object Object],[object Object],[object Object],General Features of Elimination
Alkyl Halides and Elimination Reactions ,[object Object],General Features of Elimination
The Saytzeff) Rule   (Z-rule)  According to the  Z-rule , the major product in a dehydrohalgenation is the  most stable product .
Summary ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Reference ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

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Advanced Organic Chemistry