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Chapter 16: Problem 87

Predict the stronger acid in each pair: (a) \(\mathrm{HNO}_{3}\) or HNO \(_{2}\) (b) \(\mathrm{H}_{2} \mathrm{~S}\) or \(\mathrm{H}_{2} \mathrm{O} ;\) ; (c) \(\mathrm{H}_{2} \mathrm{SO}_{4}\) or \(\mathrm{H}_{2} \mathrm{SeO}_{4}\) (d) \(\mathrm{CH}_{3} \mathrm{COOH}\) or \(\mathrm{CCl}_{3}\) ?OOH.

Short Answer

Expert verified
(a) \(HNO_3\) is the stronger acid. (b) \(H_{2}S\) is the stronger acid. (c) \(H_{2}SeO_{4}\) is the stronger acid. (d) \(CCl_{3}COOH\) is the stronger acid.

Step by step solution

01

(a) HNO\({}_{3}\) or HNO\({}_{2}\)

We will compare the stability of the resulting anions after donating a proton: - HNO\({}_{3}\) donates a proton, forming NO\({}_{3}^{-}\) anion. - HNO\({}_{2}\) donates a proton, forming NO\({}_{2}^{-}\) anion. The NO\({}_{3}^{-}\) anion is more stable due to resonance structures, which allow the negative charge to be delocalized over the entire anion. On the other hand, NO\({}_{2}^{-}\) has only one resonance structure and is less stable. Thus, \(HNO_3\) is the stronger acid.
02

(b) H\({}_{2}\)S or H\({}_{2}\)O

We will compare the strength of the O-H and S-H bonds, as well as the stability of the resulting anions: - H\({}_{2}\)O donates a proton, forming OH\(^{-}\) anion. - H\({}_{2}\)S donates a proton, forming HS\(^{-}\) anion. Sulfur is larger and less electronegative than oxygen, therefore the S-H bond is weaker than the O-H bond, making it easier for H\({}_{2}\)S to donate a proton. Additionally, HS\(^{-}\) is more stable due to the lower electronegativity and larger size of sulfur compared to oxygen. H\({}_{2}\)S is the stronger acid.
03

(c) H\({}_{2}\)SO\({}_{4}\) or H\({}_{2}\)SeO\(_{4}\)

We will compare the stability of the resulting anions after donating a proton: - H\({}_{2}\)SO\({}_{4}\) donates a proton, forming HSO\({}_{4}^{-}\) anion. - H\({}_{2}\)SeO\({}_{4}\) donates a proton, forming HSeO\({}_{4}^{-}\) anion. Selenium is larger and less electronegative than sulfur, resulting in weaker O-Se-H bonds compared to O-S-H bonds. Also, the HSeO\({}_{4}^{-}\) anion is more stable due to the larger size and lower electronegativity of selenium compared to sulfur. H\({}_{2}\)SeO\({}_{4}\) is the stronger acid.
04

(d) CH\({}_{3}\)COOH or CCl\(_{3}\)COOH

We will analyze the inductive effect of electron-withdrawing groups (EWGs) on the stability of the resulting anions: - CH\({}_{3}\)COOH donates a proton, forming CH\({}_{3}\)COO\(^{-}\) anion. - CCl\({}_{3}\)COOH donates a proton, forming CCl\({}_{3}\)COO\(^{-}\) anion. The CCl\({}_{3}\) group is a stronger electron-withdrawing group (EWG) than the CH\({}_{3}\) group due to the higher electronegativity of chlorine. The strong EWG effect of the CCl\({}_{3}\) group increases the stability of the CCl\({}_{3}\)COO\(^{-}\) anion, making it easier for CCl\({}_{3}\)COOH to donate a proton. CCl\({}_{3}\)COOH is the stronger acid.

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Most popular questions from this chapter

Write the chemical equation and the \(K_{a}\) expression for the dissociation of each of the following acids in aqueous solution. First show the reaction with \(\mathrm{H}^{+}(a q)\) as a product and then with the hydronium ion: \((\mathbf{a}) \mathrm{HNO}_{2},\) (b) \(\mathrm{ClH}_{2} \mathrm{CCOOH}\).

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) In general, the acidity of binary acids increases from left to right in a given row of the periodic table. (b) In a series of acids that have the same central atom, acid strength increases with the number of hydrogen atoms bonded to the central atom. (c) Hydrotelluric acid \(\left(\mathrm{H}_{2} \mathrm{Te}\right)\) is a stronger acid than \(\mathrm{H}_{2} \mathrm{~S}\) because Te is more electronegative than \(\mathrm{S}\).

The volume of an adult's stomach ranges from about 50 \(\mathrm{mL}\) when empty to \(1 \mathrm{~L}\) when full. If the stomach volume is \(400 \mathrm{~mL}\) and its contents have a pH of 2 , how many moles of \(\mathrm{H}^{+}\) does the stomach contain? Assuming that all the \(\mathrm{H}^{+}\) comes from \(\mathrm{HCl}\), how many grams of sodium hydrogen carbonate will totally neutralize the stomach acid?

Identify the Brønsted-Lowry acid and the Brønsted-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) \(\mathrm{HCOOH}(a q)+\mathrm{PO}_{4}^{3-}(a q) \rightleftharpoons\) $$ \mathrm{HCOO}^{-}(a q)+\mathrm{HPO}_{4}^{2-}(a q) $$

Saccharin, a sugar substitute, is a weak acid with \(\mathrm{p} K_{a}=2.32\) at \(25^{\circ} \mathrm{C}\). It ionizes in aqueous solution as follows: $$ \mathrm{HNC}_{7} \mathrm{H}_{4} \mathrm{SO}_{3}(a q) \rightleftharpoons \mathrm{H}^{+}(a q)+\mathrm{NC}_{7} \mathrm{H}_{4} \mathrm{SO}_{3}^{-}(a q) $$ What is the pH of a \(0.25 \mathrm{M}\) solution of this substance?
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