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Chapter 2: Q. 2.52 (page 87)

The ${pK}_{a}$ values of the two ammonium cations drawn below are 8.33 and 11.1. Which ${pK}_{a}$ corresponds to which cation? Explain your choice.

Short Answer

Expert verified

The compound comprising an oxygen atom will have a ${pK}_{a}$ value of 8.33 and the other compound has ${pK}_{a}$ value of 11.1.

Step by step solution

01

pKa

The ${pK}_{a}$ value shows the power of a specific acid. Acids comprising a low ${pK}_{a}$ value can easily contribute their electrons to other species.

02

To understand which acid possesses the particular pKa value

Among the two compounds, the compound containing an oxygen atom will have a ${pK}_{a}$ value of 8.33, and the other compound will have a ${pK}_{a}$ value of 11.1.

The presence of an electronegative atom like oxygen stabilizes the conjugate base by the inductive effect, which is the electron-withdrawing inductive effect.

The acidity of that particular acid increases because of the presence of the oxygen atom. So the compound possessing the oxygen atom makes the cation a stronger acid, and its ${pK}_{a}$ value will be 8.33, and the other compound will have a ${pK}_{a}$ of 11.1.

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Most popular questions from this chapter

Propranolol is an antihypertensive agent—that is, it lowers blood pressure.

a. Which proton in propranolol is most acidic? b.What products are formed when propranolol is treated with NaH? c. Which atom is most basic? d. What products are formed when propranolol is treated with HCl?

Which hydrogen in pseudoephedrine, the nasal decongestant in the commercial medication Sudafed, is most acidic?

Draw the products formed from the acid–base reaction of KOH with each compound.

a.

b.

c.

d.

Which compounds can be deprotonated by ${}^{-}{OH}$ , so that equilibrium favors the products? Refer to the pK_a table in Appendix A.

a.HCOOH

b. $H_{2} S$

c.

d. ${CH}_{3} {NH}_{2}$

Many drugs are Brønsted-Lowry acids or bases.

a. What is the most acidic proton in the analgesic ibuprofen? Draw the conjugate base.

b. What is the most basic electron pair in cocaine? Draw the conjugate acid.

See all solutions

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