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Chapter 2: Problem 13

Amide ion, \(\mathrm{H}_{2} \mathrm{~N}^{-}\), is a much stronger base than hydroxide ion, \(\mathrm{HO}^{-}\). Which is the stronger acid, \(\mathrm{NH}_{3}\) or \(\mathrm{H}_{2} \mathrm{O}\) ? Explain.

Short Answer

Expert verified
\( \mathrm{H}_{2}O \) is the stronger acid.

Step by step solution

01

Understanding the Problem

We need to compare the acid strength between ammonia \( \mathrm{NH}_{3} \) and water \( \mathrm{H}_{2}O \). This can help us determine which conjugate base is weaker. A weaker conjugate base corresponds to a stronger acid.
02

Examining Conjugate Bases

\( \mathrm{NH}_{3} \) is the conjugate acid of the amide ion (\( \mathrm{H}_{2} \mathrm{~N}^{-} \)), and \( \mathrm{H}_{2}O \) is the conjugate acid of the hydroxide ion (\( \mathrm{HO}^{-} \)). Since \( \mathrm{H}_{2} \mathrm{~N}^{-} \) is a stronger base than \( \mathrm{HO}^{-} \), it suggests that the conjugate acid of \( \mathrm{H}_{2} \mathrm{~N}^{-} \), which is \( \mathrm{NH}_{3} \), is a weaker acid compared to \( \mathrm{H}_{2}O \).
03

Conclusion on Acid Strength

The stronger base \( \mathrm{H}_{2} \mathrm{~N}^{-} \) implies its conjugate acid \( \mathrm{NH}_{3} \) is weaker than \( \mathrm{H}_{2}O \), the conjugate acid of the weaker base \( \mathrm{HO}^{-} \). Thus, \( \mathrm{H}_{2}O \) is the stronger acid between the two.

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Key Concepts

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

Amide Ion
The amide ion, represented as \( \mathrm{H}_{2} \mathrm{~N}^{-} \), is an interesting structure in acid-base chemistry. It's classified as a conjugate base, derived from the compound ammonia \( \mathrm{NH}_{3} \). This ion is characterized by the addition of an extra electron, which gives it a negative charge. This additional electron results in a very strong attraction to protons. Since it can accept a proton easily, it behaves as a strong base. Understanding how the amide ion works is vital for predicting the behavior of related compounds.
  • It's a strong base due to the presence of an extra electron.
  • It seeks to stabilize by bonding with a proton.
Amide ions play a crucial role in chemical equilibria where basic conditions are required.
Hydroxide Ion
The hydroxide ion \( \mathrm{HO}^{-} \) is a common and important ion in chemistry. It consists of a hydrogen and an oxygen atom with an extra electron, making it negatively charged. This ion is well-known for its role as a base in many chemical reactions. Its structural simplicity does not diminish its function.
  • Commonly found in bases such as sodium hydroxide \( \mathrm{NaOH} \).
  • Participates in neutralization reactions with acids.
While it is a strong base, it's not as strong as the amide ion. Its moderate base strength makes it a suitable tool in many chemical processes. The hydroxide ion serves as the conjugate base of water \( \mathrm{H}_{2}O \).
Conjugate Acids and Bases
Understanding conjugate acids and bases is essential in acid-base chemistry. A conjugate acid is formed when a base gains a proton, while a conjugate base forms when an acid loses a proton. This interconversion is crucial for reactions and equilibrium. In our context:
  • \( \mathrm{NH}_{3} \) is the conjugate acid of the amide ion \( \mathrm{H}_{2} \mathrm{~N}^{-} \).
  • \( \mathrm{H}_{2}O \) is the conjugate acid of the hydroxide ion \( \mathrm{HO}^{-} \).
These pairs show how acids and bases are related. By knowing the strength of one, you can predict the other. A stronger base typically has a weaker conjugate acid, and vice versa.
Acid Strength Comparison
Comparing acid strengths helps us predict reactivity and stability. In this exercise, we compare ammonia \( \mathrm{NH}_{3} \) and water \( \mathrm{H}_{2}O \). Since the amide ion \( \mathrm{H}_{2} \mathrm{~N}^{-} \) is a stronger base than \( \mathrm{HO}^{-} \), its conjugate acid \( \mathrm{NH}_{3} \) is weaker.
  • The weaker the conjugate base, the stronger the acid.
  • \( \mathrm{H}_{2}O \) is a stronger acid because its conjugate base \( \mathrm{HO}^{-} \) is weaker.
This comparison shows how understanding the relationship between acids and their conjugate bases can predict acidity. Water's stronger acidic nature compared to ammonia makes it an important medium in reactions. Knowing these relationships guides us in predicting chemical behavior.

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Most popular questions from this chapter

Cyclobutadiene is a rectangular molecule with two shorter double bonds and two longer single bonds. Why do the following structures not represent resonance forms?

Alcohols can act either as weak acids or as weak bases, just as water can. Show the reaction of methanol, \(\mathrm{CH}_{3} \mathrm{OH}\), with a strong acid such as \(\mathrm{HCl}\) and with a strong base \(\mathrm{such}\) as \(\mathrm{Na}^{+}-\mathrm{NH}_{2}\)

(a) The H-Cl bond length is \(136 \mathrm{pm}\). What would the dipole moment of HCl be if the molecule were \(100 \%\) ionic, \(H^{+} C l^{-} ?\) (b) The actual dipole moment of HCl is \(1.08 \mathrm{D}\). What is the percent ionic character of the \(\mathrm{H}-\mathrm{Cl}\) bond?

Calculate \(\mathrm{pK}_{\mathrm{a}}\) values from the following \(K_{\mathrm{a}}\) 's: (a) Nitromethane, \(K_{\mathrm{a}}=5.0 \times 10^{-11}\) (b) Acrylic acid, \(K_{\mathrm{a}}=5.6 \times 10^{-5}\)

Calculate \(K_{\mathrm{a}}\) values from the following \(\mathrm{pK}_{\mathrm{a}}\) 's: (a) Acetone, \(\mathrm{pK}_{\mathrm{a}}=19.3\) (b) Formic acid, \(\mathrm{pK}_{\mathrm{a}}=3.75\)
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