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Which of the indicated protons is most acidic?

User Katherin
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Final answer:

The most acidic protons are often found on positively charged species, adjacent to electronegative groups like carbonyl, and attached to highly electronegative atoms. Electronegativity and stabilization factors such as resonance strongly influence acid strength, leading to lower pKa values for more acidic protons.

Step-by-step explanation:

When determining which of the indicated protons is most acidic, we analyze several factors affecting acid strength, including the presence of a positive charge, resonance effects, and electronegativity.

Protons on a species that is positively charged are generally more acidic due to the ease of proton removal, leading to increased acid strength. Relatedly, protons adjacent to carbonyl groups (C=O), as in aldehydes, ketones, and carboxylic acids, are more acidic because of resonance stabilization of the resulting anion. This stabilization decreases the pKa value.

In the case of polyprotic acids, the strength of acidity decreases after the first proton is removed. This is because it's easier to remove a proton from a neutral species than from a negatively charged ion, which manifests as increased pKa values for subsequent protons.

Lastly, within a given period, the electronegativity of the atom to which the proton is attached also plays a crucial role: the more electronegative, the more acidic the proton.

Given this understanding, to find the most acidic proton, one should look for a positively charged species, proximity to electron-withdrawing groups like carbonyl, and attachment to more electronegative atoms.

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