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Ch.16 - Acid-Base Equilibria

Chapter 16, Problem 11a

Consider the molecular models shown here, where X represents a halogen atom. (a) If X is the same atom in both molecules, which molecule will be more acidic?

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Hey everyone, we're told that the X. In the molecular model shown below represent a halogen atom. Which molecule will be more acidic if X is the same atom for both molecules. To answer this question, let's first go ahead and draw out our conjugate bases. For A. We will have the following conjugate base and for B. R. Conjugate base will look like this. Now when we compare the two conjugate bases of each molecule, we can see that the conjugate base of B is resonance stabilized, which tells us a lot about our acidity. And because it is residents stabilized, molecule B will be more acidic in comparison to molecule A. Which in this case is not resonance stabilized. So if this is the only difference between the two, our answer here is going to be molecule B is more acidic which is going to be our final answer. Now. I hope that made sense. And let us know if you have any questions.
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Consider the molecular models shown here, where X represents a halogen atom. (b) Does the acidity of each molecule increase or decrease as the electronegativity of the atom X increases?

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