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Benzil would likely have the largest Rf value. Here's why:
Rf values and Polarity: Rf values in chromatography are a measure of how far a compound travels up a stationary phase relative to the solvent front. More polar compounds tend to interact more strongly with the stationary phase (usually silica gel), leading to lower Rf values. Less polar compounds travel further and have higher Rf values.
Polarity of the Compounds:
Benzil: Highly non-polar due to its two carbonyl groups.
Benzoin: Less polar than hydrobenzoin but more polar than benzil due to its single carbonyl group.
Hydrobenzoin: The most polar of the three due to its two hydroxyl groups.
Therefore, benzil, being the least polar, would likely show the highest Rf value in a typical TLC experiment.