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Chapter 15: Problem 20

Compounds that do not ionize in water have been known to ionize in nonaqueous solvents. In such a solvent, what would be the conjugate acid and conjugate base of methanol, \(\mathrm{CH}_{3} \mathrm{OH}\) ?

Short Answer

Expert verified
Answer: The conjugate acid of methanol is methanolium (CH3OH2+), and the conjugate base is methoxide (CH3O-).

Step by step solution

01

Understanding the Concepts of Conjugate Acid and Conjugate Base

When a Bronsted-Lowry acid loses a proton (H+), the remaining species is known as its conjugate base. Similarly, when a Bronsted-Lowry base gains a proton, the resulting species is called its conjugate acid.
02

Analyzing Methanol's Chemical Structure

Examine the structure of methanol (CH3OH). Methanol contains an oxygen atom with two lone pairs and a hydrogen atom bonded to the oxygen atom. This hydrogen atom is capable of participating in acid-base reactions.
03

Identifying Methanol as an Acid

When methanol acts as an acid, it donates a proton (H+) to a base. The oxygen atom in methanol becomes negatively charged because it retains the electrons from the O-H bond. When this happens, methanol turns into its conjugate base: CH3OH -> CH3O- + H+ The resulting ion, methoxide (CH3O-), has a negative charge and is more stable in nonaqueous solvents than in water.
04

Identifying Methanol as a Base

When methanol acts as a base, it accepts a proton (H+) from an acid. By accepting a proton, its oxygen atom forms an O-H bond, and overall methanol gains a positive charge: CH3OH + H+ -> CH3OH2+ The resulting ion, methanolium (CH3OH2+), has a positive charge and is more stable in nonaqueous solvents than in water.
05

Determining the Conjugate Acid and Conjugate Base of Methanol

Based on the ionization processes described in steps 3 and 4, the conjugate acid of methanol is methanolium (CH3OH2+) and the conjugate base of methanol is methoxide (CH3O-).

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Most popular questions from this chapter

Describe the intermolecular forces and changes in bonding that lead to the formation of a basic solution when methylamine (CH \(_{3} \mathrm{NH}_{2}\) ) dissolves in water.

Write the chemical and the net ionic equations describing the reactions that occur when aqueous solutions of these pairs of compounds are mixed together. For each reaction label the Bronsted-Lowry acids and bases. a. HCl and \(\mathrm{Ca}(\mathrm{OH})_{2}\) b. \(\mathrm{H}_{3} \mathrm{PO}_{4}\) and \(\mathrm{KOH}\) c. HNO \(_{3}\) and \(\mathrm{Na}_{2} \mathrm{CO}_{3}\) d. \(\mathrm{H}_{3} \mathrm{PO}_{4}\) and \(\mathrm{Ca}(\mathrm{OH})_{2}\)

Describe the chemical reactions of sulfur that begin with the burning of high- sulfur fossil fuel and that end with the reaction between acid rain and building exteriors made of marble \(\left(\mathrm{CaCO}_{3}\right)\)

Why is it unnecessary to publish tables of \(K_{\mathrm{b}}\) values of the conjugate bases of weak acids whose \(K_{\mathrm{a}}\) values are known?

Identify the conjugate acid of each of the following species: \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}, \mathrm{CH}_{3} \mathrm{COO}^{-}, \mathrm{HSO}_{4}^{-},\) and \(\mathrm{OH}^{-}\)
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