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Multiple Choice
Which of the following substrates will react fastest with EtOH at room temperature?
A
B
C
D
Verified step by step guidance
1
Identify the type of reaction: The reaction involves EtOH, which is a polar protic solvent, suggesting that the reaction could proceed via an SN1 mechanism.
Consider the stability of the carbocation: In an SN1 reaction, the rate-determining step is the formation of a carbocation. More stable carbocations form faster. Tertiary carbocations are more stable than secondary, which are more stable than primary.
Analyze the substituents: Electron-donating groups (EDGs) stabilize carbocations, while electron-withdrawing groups (EWGs) destabilize them. The presence of an EDG like an alkoxy group (e.g., -OCH3) can stabilize the carbocation, whereas an EWG like a nitro group (e.g., -NO2) can destabilize it.
Evaluate the given substrates: Compare the substrates based on the substituents attached to the benzene ring. Substrates with EDGs will react faster than those with EWGs due to better carbocation stabilization.
Determine the fastest reacting substrate: Based on the analysis, identify the substrate with the most favorable conditions for carbocation formation, considering both the type of carbocation and the effect of substituents.