Themes > Science > Chemistry > Organic Chemistry > Common Reaction Mechanisms > First Order Elimination: The E1 Mechanism


First Order Elimination
generally follows the following form:

 

General Mechanism: The first step requires the loss of the leaving group, forming a carbocation intermediate. A base then attacks a neighboring hydrogen forming the double bond.

Rate Equation: Rate = kr[R-X]

Points to Watch:    
   

Solvent Effects: Solvent polarity is unimportant. Works best in a good ionizing solvent
Substrate Effects: Highly substituted substrates work best 3 deg > 2 deg. Primary and methyl halides don't react.
Stereochemistry: No special stereochemistry required
Effect of Base: Base strength is unimportant because the base is not involved in the rate-determining step
Rearangements: Since E1 goes by carbocation intermediate, rearangements can occur.
Leaving Group Good leaving group required (ie. halide, tosylate, etc)


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