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Science Bowl Question

📅 MIT Science Bowl 2022🎓 HS🔄 Round 10#️⃣ Question 3🌟 BONUS📝 Multiple Choice

Electrophilic aromatic substitution on a 3-substituted indole forms a bridged tricyclic compound, where the new ring is created on the "pyrrole side". Although direct cyclization to the 2 position of the indole is a plausible mechanism, which of the following experimental techniques was used to prove that cyclization happens first to the 3 position, followed by an alkyl shift?

W) Isotopic labeling
X) Crossover experiment
Y) Kinetic isotope experiments
Z) EPR spectroscopy
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