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Toluene $\xrightarrow[\Delta ]{KMnO_4} X$ $\xrightarrow{Br_2/H_2O} Y$; $Y$ is

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What are $X$ and $Y$ in the following set of reactions?

The correct order of their reactivity towards hydrolysis at room temperature is:

Which of the following has the maximum $pK_a$ value?

$4$-Pentenoic acid when treated with $I_2$ and $NaHCO_3$ gives:

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