Which of the following compounds would react faster in an <IMAGE>
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a. E1 reaction?
b. E2 reaction?
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
E1 Reaction Mechanism
The E1 reaction is a two-step elimination process where the first step involves the formation of a carbocation intermediate after the leaving group departs. The stability of the carbocation significantly influences the reaction rate; more stable carbocations (tertiary > secondary > primary) will react faster. This mechanism is favored in polar protic solvents and typically occurs with substrates that can stabilize the positive charge.
The E2 reaction is a one-step elimination process where the base abstracts a proton while the leaving group departs simultaneously. This concerted mechanism requires a strong base and is influenced by sterics and the strength of the base. E2 reactions are favored with more hindered substrates and typically occur in polar aprotic solvents, where the base can effectively deprotonate the substrate.
Carbocation stability is a crucial factor in determining the rate of E1 reactions. Carbocations are classified based on their degree of substitution: tertiary carbocations are the most stable due to hyperconjugation and inductive effects, followed by secondary and primary. The stability of the carbocation affects the likelihood of its formation and, consequently, the overall reaction rate in E1 mechanisms.