Instead of adding to the 4a position and protonating N-5, the thiolate ion could have

Chapter 24, Problem 5

(choose chapter or problem)

Instead of adding to the 4a position and protonating N-5, the thiolate ion could have added to the 10a position and protonated N-1. Why is addition to the 4a position favored? (Hint: Which nitrogen is a stronger base?)

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