Chapter 7: Problem 78
Which of the following is the strongest acid? (a) \(\mathrm{ClO}_{3}(\mathrm{OH})\) (b) \(\mathrm{ClO}_{2}(\mathrm{OH})\) (c) \(\mathrm{SO}(\mathrm{OH})_{2}\) (d) \(\mathrm{SO}_{2}(\mathrm{OH})_{2}\)
Short Answer
Expert verified
(a) \(\mathrm{ClO}_{3}(\mathrm{OH})\) is the strongest acid.
Step by step solution
01
Understand the Acid Strength Trend
To assess the strength of an acid, understand that the strength is related to the stability of the conjugate base formed after donating a proton (H+). A more stable conjugate base corresponds to a stronger acid. Factors affecting the stability of the conjugate base include electronegativity, resonance, and the inductive effect.
02
Evaluate the Stability of Conjugate Bases
Compare the structures of the given acids to evaluate the relative stability of the conjugate bases after losing a proton. The presence of highly electronegative atoms and the possibility of resonance stabilization generally increase base stability, therefore increasing acid strength.
03
Compare Oxygen Count
Higher oxygen count in oxyacids usually means a stronger acid as more oxygens can help to stabilize the negative charge on the conjugate base through resonance and inductive effects.
04
Identify the Acid with the Most Oxygen Atoms
The compounds given are oxyacids, where a central atom is bonded to oxygen and hydrogen atoms. Typically, more oxygen atoms indicate a stronger acid because they can delocalize the negative charge more effectively. (a) has 3 oxygens, (b) has 2 oxygens, (c) has 1 oxygen, and (d) has 2 oxygens but also has a sulfur atom which is less electronegative than chlorine, suggesting it does not stabilize the negative charge as effectively as chlorine would. Therefore, more oxygen atoms leads to a conclusion that (a) \(\mathrm{ClO}_{3}(\mathrm{OH})\) is likely the strongest acid.
05
Confirm the Strongest Acid
Considering the stability of the conjugate bases, resonance structures, electronegativity, and the inductive effect, conclude that the acid with the most oxygen atoms and the most electronegative central atom will be the strongest acid among the given choices, leading to the answer being (a) \(\mathrm{ClO}_{3}(\mathrm{OH})\).
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Conjugate Base Stability
In the context of acid strength, conjugate base stability plays a pivotal role. A conjugate base is what remains of an acid after it donates a proton. The key to understanding this concept is recognizing that the more stable the conjugate base, the stronger its corresponding acid will be. This stability is often gauged by the base's ability to distribute and accommodate the negative charge left behind after the acid loses a proton.
Factors Influencing Stability
Several factors determine the stability of a conjugate base, including the electronegativity of atoms near the negative charge, the presence of resonance structures, and the inductive effect of substituent groups. By examining which bases are adept at dispersing the negative charge, we can predict the relative strength of their parent acids. In the example of oxyacids, the conjugate base with more oxygen atoms has more opportunities to delocalize the negative charge through resonance, which typically leads to increased stability and, hence, a stronger acid.Electronegativity
Electronegativity is a fundamental concept when discussing acid strength. Defined as an atom's tendency to attract electrons within a bond, electronegativity directly impacts the stability of the conjugate base. Atoms with higher electronegativity pull electron density closer, which can help stabilize additional negative charges in the conjugate base.
Electronegativity in Acid Comparison
When comparing acids, the more electronegative the atom bonded to the acidic hydrogen, the stronger the acid. In the given exercise, chlorine is more electronegative than sulfur, which suggests that acids with chlorine as the central atom are generally stronger than those with sulfur, given comparable structures.Resonance Stabilization
Resonance stabilization is another crucial factor affecting acid strength. Resonance occurs when the electron distribution within a molecule can be represented by two or more valid Lewis structures. These structures, called resonance structures, delocalize negative charges over several atoms, reducing the electron density on any single atom and thus stabilizing the conjugate base.
Resonance and Acidity
Acids whose conjugate bases have resonance stabilization are typically stronger because the spread-out charge is less repulsive, making it easier for the base to exist without reverting to its acid form. In the exercise, when analyzing which conjugate base is most stabilized by resonance, the central atom connected to multiple highly electronegative oxygens will likely provide the most resonance stabilization, leading to a strong acid.Inductive Effect
The inductive effect refers to the influence of polar bonds on the distribution of electrons in a molecule. It has a considerable impact on acid strength, particularly in molecules where electronegative elements are present.
Understanding Inductive Effects
Electronegative atoms can pull electron density toward themselves through sigma bonds. This withdrawal of electron density can help stabilize the negative charge on a conjugate base, effectively increasing the parent acid's strength. In our exercise, oxyacids with more oxygen atoms bonded to the central atom would exhibit a stronger inductive effect, leading to increased acid strength.Oxyacid Acid Strength
Focusing on oxyacids, their strength is largely determined by the number of oxygen atoms bonded to the central atom. Oxygen's high electronegativity and its ability to participate in resonance stabilization make it a key player in this determination.
Oxyacids and Their Strength
Generally, the more oxygen atoms present, the more strongly the negative charge is delocalized over the molecule, resulting in a stronger acid. The exercise addresses oxyacids, and we can see that \(\mathrm{ClO}_{3}(\mathrm{OH})\) with three oxygens likely represents the strongest acid because it can spread its charge most efficiently across multiple electronegative oxygen atoms.Comparing Acid Strengths
When comparing acid strengths, it's essential to consider several factors: the stability of the conjugate base, resonance structures, the central atom's electronegativity, and the inductive effect. By systematically evaluating each of these aspects, we can determine the strongest acid among a given set.