Motivated by results about “untangling” closed curves on hyperbolic surfaces, Gupta and Kapovich introduced the primitivity and simplicity index functions for finitely generated free groups, and , where , and obtained some upper and lower bounds for these functions. In this paper, we study the behavior of the sequence as . Answering a question of Kapovich, we prove that this sequence is unbounded and that for , we have . By contrast, we show that for all , one has . In addition to topological and group-theoretic arguments, number-theoretic considerations, particularly the use of asymptotic properties of the second Chebyshev function, turn out to play a key role in the proofs.

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