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Ephedrine, a central nervous system stimulant, is used in nasal sprays as a decongestant. This compound is a weak organic base: $$ \mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ON}(a q)+\mathrm{H}_{2} \mathrm{O}(l) \rightleftharpoons \mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ONH}^{+}(a q)+\mathrm{OH}^{-}(a q) $$ A \(0.035 \mathrm{M}\) solution of ephedrine has a \(\mathrm{pH}\) of 11.33 . (a) What are the equilibrium concentrations of \(\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ON}, \mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ONH}^{+},\) and \(\mathrm{OH}^{-} ?\) (b) Calculate \(K_{b}\) for ephedrine.

Short Answer

Expert verified
The equilibrium concentrations are 0.03286 M for C10H15ON, 2.14 x 10^-3 M for C10H15ONH^+, and OH^-. Kb is 1.39 x 10^-4.

Step by step solution

01

Define the Equilibrium Expression

The equilibrium expression for this weak base is given by the equation:\[ \mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ON}(aq) + \mathrm{H}_2\mathrm{O}(l) \rightleftharpoons \mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ONH}^+(aq) + \mathrm{OH}^-(aq) \]The equilibrium constant expression, \(K_b\), is:\[ K_b = \frac{[\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ONH}^+][\mathrm{OH}^-]}{[\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ON}]} \]
02

Calculate [OH鈦籡 from pH

Since the pH of the solution is 11.33, we first find the pOH:\[ \text{pOH} = 14 - \text{pH} = 14 - 11.33 = 2.67 \]Now, calculate the hydroxide ion concentration, \([\mathrm{OH}^-]\):\[ [\mathrm{OH}^-] = 10^{-\text{pOH}} = 10^{-2.67} \approx 2.14 \times 10^{-3} \text{ M} \]
03

ICE Table to Find Equilibrium Concentrations

Create an ICE table based on the initial concentration, change, and equilibrium concentrations for the substances involved:- Initial: \( [\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ON}] = 0.035 \text{ M}, [\mathrm{OH}^-] = 0, [\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ONH}^+] = 0 \)- Change: \(-x, +x, +x\)- Equilibrium: \(0.035 - x, x, x\)Given \([\mathrm{OH}^-] = 2.14 \times 10^{-3} \text{ M}\), we set \(x = 2.14 \times 10^{-3}\).
04

Calculate Equilibrium Concentrations

Using the value of \(x = 2.14 \times 10^{-3} \text{ M}\), find the equilibrium concentrations:\[ [\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ONH}^+] = x = 2.14 \times 10^{-3} \text{ M} \]\[ [\mathrm{OH}^-] = x = 2.14 \times 10^{-3} \text{ M} \]\[ [\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ON}] = 0.035 - 2.14 \times 10^{-3} = 0.03286 \text{ M} \]
05

Calculate Kb for Ephedrine

Substitute the equilibrium concentrations into the \(K_b\) expression:\[ K_b = \frac{(2.14 \times 10^{-3})(2.14 \times 10^{-3})}{0.03286} = \frac{4.58 \times 10^{-6}}{0.03286} \approx 1.39 \times 10^{-4} \]

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Equilibrium Constant Expression
When discussing weak base equilibrium, such as the reaction involving ephedrine, it's important to understand what an equilibrium constant expression is. This expression allows us to quantify the state of equilibrium in a chemical reaction. For our reaction \( \mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ON}(aq) + \mathrm{H}_2\mathrm{O}(l) \rightleftharpoons \mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ONH}^+(aq) + \mathrm{OH}^-(aq) \), the equilibrium constant, known as the basicity constant \( K_b \), is expressed as:
  • \( K_b = \frac{[\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ONH}^+][\mathrm{OH}^-]}{[\mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ON}]} \)
In this expression, each component represents the concentration of that species at equilibrium. Larger values of \( K_b \) indicate a stronger base, meaning it dissociates more in solution, while smaller values suggest a weaker base.
pH and pOH Calculations
Calculating pH and pOH is crucial for understanding the properties of a solution. The pH scale measures how acidic or basic a solution is, with lower pH values indicating more acidic solutions and higher pH values indicating more basic. In the case of bases, like our ephedrine solution, we often deal with pOH. Here's how to calculate it:
  • Start with the solution's pH. For ephedrine, the pH is given as 11.33.
  • The relationship between pH and pOH is \( \text{pOH} = 14 - \text{pH} \).
  • Substitute the pH into this equation: \( \text{pOH} = 14 - 11.33 = 2.67 \).
  • From the pOH, determine the hydroxide concentration with: \( [\mathrm{OH}^-] = 10^{-\text{pOH}} \).
  • For a pOH of 2.67, \( [\mathrm{OH}^-] \approx 2.14 \times 10^{-3} \text{ M} \).
These calculations are key to linking the pH of a given solution to the concentration of hydroxide ions, helping us to track how bases interact in solution.
ICE Table Method
The ICE Table is a powerful tool in calculating equilibrium concentrations. It stands for Initial, Change, and Equilibrium. Let's break down how this method works using ephedrine:
  • Initial: Start by laying out the initial concentrations before any reaction takes place. For ephedrine, it鈥檚 given as a \(0.035 \text{ M}\) solution.
  • Change: Identify how concentrations change during the reaction. Represent these changes with the variable, \(x\). In this case, as ephedrine forms \( \mathrm{C}_{10} \mathrm{H}_{15} \mathrm{ONH}^+ \) and \( \mathrm{OH}^- \), their concentrations increase by \(x\), while the initial compound subtracts \(x\).
  • Equilibrium: Solve for \(x\) and adjust the initial concentrations to reflect equilibrium by adding or subtracting \(x\) accordingly.
For ephedrine, \(x\) was found to be \(2.14 \times 10^{-3} \text{ M}\), allowing us to determine the equilibrium concentrations of the involved species.
Basicity Constant
A key characteristic of organic bases like ephedrine is the basicity constant \(K_b\). This constant measures the strength of a base in a solution. The stronger the base, the larger its \(K_b\) value. To calculate \(K_b\) for ephedrine:
  • Use the equilibrium concentrations discovered from the ICE table method.
  • Substitute these into the \(K_b\) expression: \( K_b = \frac{(2.14 \times 10^{-3})(2.14 \times 10^{-3})}{0.03286} \)
  • Calculate to find \( K_b \approx 1.39 \times 10^{-4} \).
This constant helps us compares ephedrine's ability to create hydroxide ions in solution compared to other bases.
Organic Base Chemistry
Organic base chemistry delves into the behavior of compounds containing basic functional groups within an organic framework. These typically include nitrogen atoms with lone pairs, often depicted in amines. In the context of ephedrine, understanding its weak base nature helps predict how it behaves in aqueous environments. Consider the following features of organic bases:
  • They frequently participate in equilibrium with water, accepting protons to form hydroxide ions.
  • Their basic strength is quantifiable by \( K_b \), a specific equilibrium constant.
  • Because they are organic, they involve carbon-based molecular structures, influencing physical and chemical properties.
By knowing these aspects, we gain deeper insight not only into ephedrine but a broader range of organic bases in chemistry.

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Most popular questions from this chapter

Identify the Lewis acid and Lewis base in each of the following reactions: (a) \(\mathrm{HNO}_{2}(a q)+\mathrm{OH}^{-}(a q) \rightleftharpoons \mathrm{NO}_{2}^{-}(a q)+\mathrm{H}_{2} \mathrm{O}(l)\) (b) \(\mathrm{FeBr}_{3}(s)+\mathrm{Br}^{-}(a q) \rightleftharpoons \mathrm{FeBr}_{4}^{-}(a q)\) (c) \(\mathrm{Zn}^{2+}(a q)+4 \mathrm{NH}_{3}(a q) \rightleftharpoons \mathrm{Zn}\left(\mathrm{NH}_{3}\right)_{4}{ }^{2+}(a q)\) (d) \(\mathrm{SO}_{2}(\mathrm{~g})+\mathrm{H}_{2} \mathrm{O}(l) \rightleftharpoons \mathrm{H}_{2} \mathrm{SO}_{3}(a q)\)

Indicate whether each of the following statements is true or false. For each statement that is false, correct the statement to make it true. (a) Acid strength in a series of \(\mathrm{H}-\) A molecules increases with increasing size of \(\mathrm{A} .(\mathbf{b})\) For acids of the same general structure but differing electronegativities of the central atoms, acid strength decreases with increasing electronegativity of the central atom. (c) The strongest acid known is HF because fluorine is the most electronegative element.

Which, if any, of the following statements are true? (a) The stronger the base, the smaller the \(\mathrm{p} K_{b}\). (b) The stronger the base, the larger the \(\mathrm{p} K_{b}\). (c) The stronger the base, the smaller the \(K_{b}\). (d) The stronger the base, the larger the \(K_{b}\). (e) The stronger the base, the smaller the \(\mathrm{p} K_{a}\) of its conjugate acid. (f) The stronger the base, the larger the \(\mathrm{pK}_{a}\) of its conjugate acid.

Identify the Br酶nsted-Lowry acid and the Br酶nsted-Lowry base on the left side of each of the following equations, and also identify the conjugate acid and conjugate base of each on the right side: (a) \(\mathrm{NH}_{4}^{+}(a q)+\mathrm{CN}^{-}(a q) \rightleftharpoons \mathrm{HCN}(a q)+\mathrm{NH}_{3}(a q)\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}(a q)+\mathrm{H}_{2} \mathrm{O}(l) \rightleftharpoons\) $$ \left(\mathrm{CH}_{3}\right)_{3} \mathrm{NH}^{+}(a q)+\mathrm{OH}^{-}(a q) $$ (c) \(\mathrm{HCOOH}(a q)+\mathrm{PO}_{4}^{3-}(a q) \rightleftharpoons\) $$ \mathrm{HCOO}^{-}(a q)+\mathrm{HPO}_{4}^{2-}(a q) $$

Label each of the following as being a strong base, a weak base, or a species with negligible basicity. In each case write the formula of its conjugate acid, and indicate whether the conjugate acid is a strong acid, a weak acid, or a species with negligible acidity: \((\mathbf{a}) \mathrm{F}^{-}(\mathbf{b}) \mathrm{Br}^{-}(\mathbf{c}) \mathrm{HS}^{-}(\mathbf{d}) \mathrm{ClO}_{4}^{-}(\mathbf{e}) \mathrm{HCOO}^{-}\)

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