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Which should be the stronger acid, HOCN or HCN? Explain briefly. (In HOCN, the \(\mathrm{H}^{+}\) ion is attached to the \(\mathrm{O}\) atom of the \(\mathrm{OCN}^{-}\) ion.)

Short Answer

Expert verified
HOCN is stronger because it releases H鈦 more easily due to the more polar O-H bond.

Step by step solution

01

Understand the Compounds

HOCN and HCN are both acids, but they differ in their molecular structure. In HOCN, the hydrogen ion (H鈦) is bonded to the oxygen atom, while in HCN, it is bonded directly to the carbon atom.
02

Consider Atomic Electronegativities

Oxygen is more electronegative than carbon. This means that in HOCN, the O-H bond is more polar because oxygen attracts electrons more strongly than carbon, making it easier for H鈦 to dissociate from the molecule.
03

Assess Acid Strength

A stronger acid has a greater tendency to donate its hydrogen ion (H鈦). In HOCN, because the O-H bond is more polar, the H鈦 is more easily released, suggesting that HOCN should be the stronger acid compared to HCN.

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Key Concepts

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

Molecular Structure and Acid Strength
Molecular structure is a key factor in determining the strength of an acid. The arrangement of atoms in a molecule dictates how easily the hydrogen ion (H鈦) is released. In the case of HOCN and HCN, both are acids, yet they differ in their molecular structure.

In HOCN, the hydrogen ion is bonded to an oxygen atom, whereas, in HCN, the hydrogen is attached to a carbon atom. This structural difference significantly impacts their acid strength. The bond between hydrogen and oxygen in HOCN forms an O-H bond, a feature common in strong acids.

The molecular structure affects the acid's ability to dissociate in a solution. The more readily an acid donates its H鈦 ion, the stronger the acid. In general, acids with a highly electronegative element bonded to the hydrogen tend to release H鈦 more easily.
Electronegativity and Its Role in Acid Strength
Electronegativity refers to an atom's ability to attract and hold onto electrons. It plays a crucial role in determining the polarity of a bond and, consequently, the acid鈥檚 strength.

In comparing HOCN and HCN, the O-H bond in HOCN is more polar than the C-H bond in HCN because oxygen is more electronegative than carbon.
  • Oxygen pulls the shared electrons closer to itself, creating an uneven electron distribution.
  • This makes it easier for the H鈦 ion in HOCN to dissociate, increasing the acid's strength.

Acids with higher electronegative atoms bonded to hydrogen usually show increased acidity because the bond becomes more polar. This polarization facilitates the release of H鈦 ions. Therefore, the higher electronegativity of oxygen compared to carbon is a major reason why HOCN is a stronger acid than HCN.
Bond Polarity and Its Impact on Acid Dissociation
Bond polarity is an important concept in understanding how acids dissociate to release hydrogen ions. A polar bond has electrons shared unequally between two atoms, leading to a partial positive and negative charge.

The oxygen-hydrogen bond in HOCN is highly polar due to the significant electronegativity difference between oxygen and hydrogen.
  • This polarity facilitates the breaking of the O-H bond, which is crucial for the acid to release its H鈦 ion.
  • The more polar the bond, the weaker it typically becomes, making it easier for the hydrogen ion to dissociate.

On the other hand, the C-H bond in HCN exhibits much lower polarity, requiring more energy to break and release the H鈦 ion. This reduced polarity makes HCN a weaker acid compared to HOCN.

Overall, increased bond polarity generally correlates with higher acid strength due to the ease of hydrogen ion dissociation.

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Most popular questions from this chapter

Calculate the hydronium ion concentration and \(\mathrm{pH}\) of the solution that results when 22.0 mL of 0.15 M acetic acid, \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H},\) is mixed with \(22.0 \mathrm{mL}\) of \(0.15 \mathrm{M} \mathrm{NaOH}\).

Perchloric acid behaves as an acid, even when it is dissolved in sulfuric acid. (a) Write a balanced equation showing how perchloric acid can transfer a proton to sulfuric acid. (b) Draw a Lewis electron dot structure for sulfuric acid. How can sulfuric acid function as a base?

Several acids are listed here with their respective equilibrium constants: $$\begin{aligned}&\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}(\mathrm{aq})+\mathrm{H}_{2} \mathrm{O}(\ell) \rightleftarrows \mathrm{H}_{3} \mathrm{O}^{+}(\mathrm{aq})+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}(\mathrm{aq})\\\&K_{\mathrm{a}}=1.3 \times 10^{-10}\end{aligned}$$ $$\begin{aligned}&\mathrm{HCO}_{2} \mathrm{H}(\mathrm{aq})+\mathrm{H}_{2} \mathrm{O}(\ell) \rightleftarrows \mathrm{H}_{3} \mathrm{O}^{+}(\mathrm{aq})+\mathrm{HCO}_{2}^{-}(\mathrm{aq})\\\&K_{\mathrm{a}}=1.8 \times 10^{-4} \end{aligned}$$ $$\begin{aligned}&\mathrm{HC}_{2} \mathrm{O}_{4}^{-}(\mathrm{aq})+\mathrm{H}_{2} \mathrm{O}(\ell) \rightleftarrows \mathrm{H}_{3} \mathrm{O}^{+}(\mathrm{aq})+\mathrm{C}_{2} \mathrm{O}_{4}^{2-}(\mathrm{aq})\\\&K_{\mathrm{a}}=6.4 \times 10^{-5}\end{aligned}$$ (a) Which is the strongest acid? Which is the weakest acid? (b) Which acid has the weakest conjugate base? (c) Which acid has the strongest conjugate base?

Methylamine, \(\mathrm{CH}_{3} \mathrm{NH}_{2},\) is a weak base. $$\mathrm{CH}_{3} \mathrm{NH}_{2}(\mathrm{aq})+\mathrm{H}_{2} \mathrm{O}(\ell) \rightleftarrows \mathrm{CH}_{3} \mathrm{NH}_{3}^{+}(\mathrm{aq})+\mathrm{OH}^{-}(\mathrm{aq})$$ If the pH of a 0.065 M solution of the amine is 11.70 what is the value of \(K_{\mathrm{b}} ?\)

A saturated solution of milk of magnesia, \(\mathrm{Mg}(\mathrm{OH})_{2},\) has a pH of \(10.52 .\) What is the hydronium ion concentration of the solution? What is the hydroxide ion concentration? Is the solution acidic or basic?

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