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Alcohols are very weak acids, therefore they cannot react with strong bases. the conclusion i formed from this was: very low acid / base strength leads to not being able to react with stronger bases / acids. But then, while reading the chapter about Amines, i read that aromatic amines (such as aniline) ONLY react with strong acids. Therefore my question is: Why is it that very weak acids cannot interact with strong bases, however very weak bases can ONLY interact with strong acids?

User Deandob
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Final answer:

The reactivity of weak acids and bases with counterparts is dictated by their tendency to form weaker conjugate species. Weak acids do not react significantly with strong bases because their conjugate bases are too competitive, whereas very weak bases like aromatic amines require strong acids due to the stability of their resulting conjugate acids.

Step-by-step explanation:

Alcohols are weak acids and do not react significantly with strong bases because their conjugate bases are strong and compete effectively with hydroxide ions.

On the other hand, very weak bases like aromatic amines require strong acids to become protonated because their conjugate acids are weak.

This means that the interaction with a strong acid is necessary to pull the lone pair of electrons on the nitrogen into a covalent bond with a hydrogen ion (proton), forming the conjugate acid.

Amines react with water to produce hydroxide ions, albeit in small amounts, which is a property reflecting their weak basic nature. When reacting with a strong acid, amines are converted into their conjugate acids (e.g., aniline to anilinium ion), which are a lower energy, more stable form.

Understanding this concept involves recognizing that the strength of acids and bases is relative and that equilibrium favors the formation of the weaker acid and base in a reaction.

The Brønsted-Lowry acid-base theory provides a framework for understanding these interactions, by which ions and molecules can act as acids (proton donors) or bases (proton acceptors) depending on the reaction context.

User Karl Nicoll
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