Salicylic acid, HOC6H4CO2H, and its derivatives have been used as pain relievers for a long time. Salicylic acid occurs in small amounts in the leaves, bark, and roots of some vegetation (most notably historically in the barkof the willow tree). Extracts of these plants have been used as medications for centuries. The acid was first isolated in the laboratory in 1838.(a) Both functional groups of salicylic acid ionize in water, with Ka = 1.0 × 10−3 for the—CO2H group and 4.2 × 10−13 for the −OH group. What is the pH of a saturated solution of the acid (solubility = 1.8 g/L).(b) Aspirin was discovered as a result of efforts to produce a derivative of salicylic acid that would not be irritating to the stomach lining. Aspirin is acetylsalicylic acid, CH3CO2C6H4CO2H. The −CO2H functional group is stillpresent, but its acidity is reduced, Ka = 3.0 × 10−4. What is the pH of a solution of aspirin with the same concentration as a saturated solution of salicylic acid (See Part a).(c) Under some conditions, aspirin reacts with water and forms a solution of salicylic acid and acetic acid: CH3 CO2 C6 H4 CO2 H(aq) + H2 O(l) ⟶ HOC6 H4 CO2 H(aq) + CH3 CO2 H(aq)i. Which of the acids, salicylic acid or acetic acid, produces more hydronium ions in such a solution?ii. What are the concentrations of molecules and ions in a solution produced by the hydrolysis of 0.50 g of aspirin dissolved in enough water to give 75 mL of solution?

Principles of Modern Chemistry
8th Edition
ISBN:9781305079113
Author:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Publisher:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Chapter15: Acid–base Equilibria
Section: Chapter Questions
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Salicylic acid, HOC6H4CO2H, and its derivatives have been used as pain relievers for a long time. Salicylic acid occurs in small amounts in the leaves, bark, and roots of some vegetation (most notably historically in the bark
of the willow tree). Extracts of these plants have been used as medications for centuries. The acid was first isolated in the laboratory in 1838.
(a) Both functional groups of salicylic acid ionize in water, with Ka = 1.0 × 10−3 for the—CO2H group and 4.2 × 10−13 for the −OH group. What is the pH of a saturated solution of the acid (solubility = 1.8 g/L).
(b) Aspirin was discovered as a result of efforts to produce a derivative of salicylic acid that would not be irritating to the stomach lining. Aspirin is acetylsalicylic acid, CH3CO2C6H4CO2H. The −CO2H functional group is still
present, but its acidity is reduced, Ka = 3.0 × 10−4. What is the pH of a solution of aspirin with the same concentration as a saturated solution of salicylic acid (See Part a).
(c) Under some conditions, aspirin reacts with water and forms a solution of salicylic acid and acetic acid: CH3 CO2 C6 H4 CO2 H(aq) + H2 O(l) ⟶ HOC6 H4 CO2 H(aq) + CH3 CO2 H(aq)
i. Which of the acids, salicylic acid or acetic acid, produces more hydronium ions in such a solution?
ii. What are the concentrations of molecules and ions in a solution produced by the hydrolysis of 0.50 g of aspirin dissolved in enough water to give 75 mL of solution?

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