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Reaction rates of strained cycloalkynes and cycloalkenes with 1,2‐quinone were quantified by stopped flow UV‐Vis spectroscopy and computational analysis. We found that the strained alkyne BCN−OH 3 (k2 1824 M−1 s−1) reacts >150 times faster than the strained alkene TCO‐OH 5 (k2 11.56 M−1 s−1), and that derivatization with a carbamate can lead to a reduction of the rate constant with almost half...