Chapter5: Some Reactions From Biochemistry
Section: Chapter Questions
Problem 11EQ
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Question
When naphthalene undergoes an irreversible electrophilic
which proceeds through the most stable arenium ion intermediate. In
Section 23.7, we mentioned that substitution is generally favored at the α
position over the β position, which means that the arenium ion is more stable when the electrophile attaches to the α position. Explain this difference in arenium ion stabilities. Hint: Draw out all
resonance structures for each arenium ion intermediate. Does each one have the same number of resonance
structures? How many resonance structures of each intermediate preserve the aromaticity?
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