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Ch.16 - Acid-Base Equilibria
Chapter 16, Problem 111

Ritalin is the trade name of a drug, methylphenidate, used to treat attention-deficit/hyperactivity disorder in young adults. The chemical structure of methylphenidate is Chemical structure of ibuprofen, a common pain reliever.
(a) Is Ritalin an acid or a base? An electrolyte or a nonelectrolyte?

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1
Step 1: Identify the functional groups in the chemical structure of methylphenidate. Look for groups that can donate or accept protons (H+).
Step 2: Determine if the molecule has any acidic or basic functional groups. Acids typically have carboxyl groups (-COOH), while bases often have amine groups (-NH2).
Step 3: Assess the molecule's ability to dissociate in water. Electrolytes dissociate into ions in water, while nonelectrolytes do not.
Step 4: Compare the structure of methylphenidate to known acids, bases, electrolytes, and nonelectrolytes to make an informed decision.
Step 5: Conclude whether Ritalin (methylphenidate) is an acid or a base, and whether it is an electrolyte or a nonelectrolyte based on the functional groups and dissociation properties.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acids and Bases

Acids are substances that can donate protons (H+) in a solution, while bases can accept protons. The strength of an acid or base is determined by its ability to dissociate in water. Understanding whether a compound behaves as an acid or a base is crucial for predicting its reactivity and interactions in biological systems.
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Electrolytes

Electrolytes are substances that dissociate into ions when dissolved in water, allowing the solution to conduct electricity. Strong electrolytes completely dissociate, while weak electrolytes partially dissociate. Identifying whether a compound is an electrolyte or nonelectrolyte is important for understanding its behavior in physiological conditions and its effects on cellular functions.
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Chemical Structure and Functional Groups

The chemical structure of a compound, including its functional groups, determines its chemical properties and biological activity. For example, the presence of carboxylic acid groups (-COOH) can indicate acidic behavior, while amine groups (-NH2) can suggest basic properties. Analyzing the structure of methylphenidate is essential for determining its classification as an acid or base and its electrolyte nature.
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Related Practice
Textbook Question

Butyric acid is responsible for the foul smell of rancid butter. The pKa of butyric acid is 4.84. (a) Calculate the pKb for the butyrate ion.

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Textbook Question

Butyric acid is responsible for the foul smell of rancid butter. The pKa of butyric acid is 4.84. (b) Calculate the pH of a 0.050 M solution of butyric acid.

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Textbook Question

Butyric acid is responsible for the foul smell of rancid butter. The pKa of butyric acid is 4.84. (c) Calculate the pH of a 0.050 M solution of sodium butyrate.

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Textbook Question

The following observations are made about a diprotic acid H2A: (i) A 0.10 M solution of H2A has pH = 3.30. (ii) A 0.10 M solution of the salt NaHA is acidic. Which of the following could be the value of pKa2 for H2A: (i) 3.22, (ii) 5.30, (iii) 7.47, or (iv) 9.82?

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Open Question
Many moderately large organic molecules containing basic nitrogen atoms are not very soluble in water as neutral molecules, but they are frequently much more soluble as their acid salts. Assuming that the pH in the stomach is 2.5, indicate whether each of the following compounds would be present in the stomach as the neutral base or in the protonated form: nicotine, Kb = 7 * 10-7; caffeine, Kb = 4 * 10-14; strychnine, Kb = 1 * 10-6; quinine, Kb = 1.1 * 10-6.
Textbook Question

The amino acid glycine 1H2N¬CH2¬COOH2 can participate in the following equilibria in water: H2N¬CH2¬COOH + H2OΔ H2N¬CH2¬COO- + H3O+ Ka = 4.3 * 10-3 H2N¬CH2¬COOH + H2OΔ+H3N¬CH2¬COOH + OH- Kb = 6.0 * 10-5 (a) Use the values of Ka and Kb to estimate the equilibrium constant for the intramolecular proton transfer to form a zwitterion: H2N¬CH2¬COOH Δ +H3N¬CH2¬COO-

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