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What is the expected acidity of a molecule that contains a carboxylic acid (-COOH) functional group and a tertiary amine (-NR3) functional group? Provide a brief explanation to justify your answer.

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The expected acidity of a molecule containing both a carboxylic acid  -COOH  functional group and a tertiary amine  -NR3  functional group would be moderately acidic. This is because the carboxylic acid group is acidic, while the tertiary amine group is basic.The carboxylic acid group  -COOH  has a pKa value typically ranging from 4 to 5, which means it can donate a proton  H+  in solution, making the solution acidic. The acidic nature of carboxylic acids is due to the resonance stabilization of the conjugate base  carboxylate anion  after losing a proton.On the other hand, the tertiary amine group  -NR3  is basic, as it has a lone pair of electrons on the nitrogen atom that can accept a proton  H+ . However, tertiary amines are generally weaker bases compared to primary and secondary amines, due to steric hindrance and electron-donating alkyl groups, which reduce the availability of the lone pair for protonation.In a molecule containing both functional groups, the acidic carboxylic acid group will dominate the overall acidity of the molecule. However, the presence of the basic tertiary amine group may slightly reduce the acidity compared to a molecule with only a carboxylic acid group. Therefore, the expected acidity of such a molecule would be moderately acidic, with the carboxylic acid group being the primary contributor to the acidity.
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