Hydroxyl radicals can pluck hydrogen atoms from molecules ("hydrogen abstraction"), and hydroxide ions can pluck protons from molecules ("deprotonation"). Write the reaction equations and Lewis dot structures for the hydrogen abstraction and deprotonation reactions for the generic carboxylic acid \(\mathrm{R}-\mathrm{COOH}\) with hydroxyl radical and hydroxide ion, respectively. Why is hydroxyl radical more toxic to living systems than hydroxide ion?

The reaction equations and the Lewis dot structures for hydrogen abstraction and deprotonation of a generic carboxylic acid with hydroxyl radical and hydroxide ion can be represented as: Hydrogen Abstraction: \( \mathrm{HO} \cdot + \mathrm{R}-\mathrm{COOH} \rightarrow \mathrm{H_2O} + \mathrm{R}-\mathrm{COO} \cdot \) Lewis dot structures: \(\mathrm{HO} \cdot\), \(\mathrm{R} \equiv \stackrel{\displaystyle \mathrm{O}}{\mathrm{C}}-\stackrel{\displaystyle \mathrm{O}}{\mathrm{H}}\), \(\mathrm{H}\stackrel{\displaystyle \mathrm{O}}{\mathrm{H}}\), \(\mathrm{R}\equiv \stackrel{\displaystyle \mathrm{O}}{\mathrm{C}}-\mathrm{O} \cdot\) Deprotonation: \( \mathrm{OH}^- + \mathrm{R}-\mathrm{COOH} \rightarrow \mathrm{H_2O} + \mathrm{R}-\mathrm{COO}^-\) Lewis dot structures: \(\mathrm{\stackrel{\displaystyle O}{H}}^-\), \(\mathrm{R} \equiv \stackrel{\displaystyle \mathrm{O}}{\mathrm{C}}-\stackrel{\displaystyle \mathrm{O}}{\mathrm{H}}\), \(\mathrm{H}\stackrel{\displaystyle \mathrm{O}}{\mathrm{H}}\), \(\mathrm{R} \equiv \stackrel{\displaystyle \mathrm{O}}{\mathrm{C}}-\mathrm{O}^- \equiv\) Hydroxyl radicals are more toxic to living systems compared to hydroxide ions due to their high reactivity caused by the presence of an unpaired electron, making them strong oxidizing agents capable of causing widespread cellular damage. Meanwhile, hydroxide ions are less reactive and participate in controlled reactions, hence less toxic to living systems.