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Chapter 4: Problem 12

Each molecule or ion can function as a base. Write a structural formula of the conjugate acid formed by reaction of each with \(\mathrm{HCl}\). (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{HCH}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (d) \(\mathrm{HCO}_{3}{ }^{-}\)

Short Answer

Expert verified
Question: Identify the conjugate acid formed by the reaction of each of the following molecules or ions with HCl: (a) CH3CH2OH, (b) HCH, (c) (CH3)2NH, (d) HCO3−. Answer: (a) The conjugate acid formed after the reaction of CH3CH2OH with HCl is CH3CH2OH2+. (b) The conjugate acid formed after the reaction of HCH with HCl is H2CH+. (c) The conjugate acid formed after the reaction of (CH3)2NH with HCl is (CH3)2NH2+. (d) The conjugate acid formed after the reaction of HCO3- with HCl is H2CO3.

Step by step solution

01

(a) Reaction of CH3CH2OH with HCl

The oxygen atom on the OH group in \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{OH}\) can act as a base, accepting a proton (H+). After accepting a proton, the resulting molecule will look like this: \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{OH}_{2}^{+}\) which is the conjugate acid.
02

(b) Reaction of HCH with HCl

In this case, the carbon atom in \(\mathrm{HCH}\) is the one that can act as a base. After reacting with HCl, a proton will be added to the carbon atom, and the conjugate acid will be \(\mathrm{H}_{2}\mathrm{C}\mathrm{H}^{+}\).
03

(c) Reaction of (CH3)2NH with HCl

The nitrogen atom in \(\left(\mathrm{CH}_{3}\right)_{2}\mathrm{NH}\) acts as a base by accepting a proton (H+) from HCl. The conjugate acid formed after the reaction will be \(\left(\mathrm{CH}_{3}\right)_{2}\mathrm{NH}_{2}^{+}\).
04

(d) Reaction of HCO3- with HCl

The oxygen atom with a negative charge in \(\mathrm{HCO}_{3}^{-}\) can act as a base and accept a proton from HCl. After reacting with HCl, the conjugate acid will be \(\mathrm{H}_{2}\mathrm{CO}_{3}\).

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Most popular questions from this chapter

Methyl isocyanate, \(\mathrm{CH}_{3}-\mathrm{N}=\mathrm{C}=\mathrm{O}\), is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 persons were exposed to its vapors, and over 2000 of these people died. (a) Write a Lewis structure for methyl isocyanate, and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom? (b) Methyl isocyanate reacts with strong acids, such as sulfuric acid, to form a cation. Will this molecule undergo protonation more readily on its oxygen or nitrogen atom? In considering contributing structures to each hybrid, do not consider structures in which more than one atom has an incomplete octet.

Account for the fact that nitroacetic acid, \(\mathrm{O}_{2} \mathrm{NCH}_{2} \mathrm{COOH}\left(\mathrm{p} K_{\mathrm{a}} 1.68\right)\), is a considerably stronger acid than acetic acid, \(\mathrm{CH}_{3} \mathrm{COOH}\left(\mathrm{p} K_{\mathrm{a}} 4.76\right)\).

Label the most acidic hydrogen in each molecule, and justify your choice by using appropriate \(\mathrm{p} K_{\mathrm{a}}\) values. (a) \(\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (b) \(\mathrm{HSCH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (c) \(\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}\) (d) \(\mathrm{HOCCH}_{2} \mathrm{CH}_{2} \mathrm{SH}\) (e) \(\mathrm{CH}_{3} \mathrm{CHCOH}_{\mathrm{CH}}^{\mathrm{HO}}\) (f) \(\mathrm{H}_{3} \mathrm{NCH}_{2} \mathrm{CH}_{2} \|_{\mathrm{COH}}^{\mathrm{O}}\) (g) \(\mathrm{H}_{3} \mathrm{NCH}_{2} \mathrm{CH}_{2} \|_{\mathrm{CO}^{-}}\) (h) \(\mathrm{HSCH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

Offer an explanation for the following observations. (a) \(\mathrm{H}_{3} \mathrm{O}^{+}\)is a stronger acid than \(\mathrm{NH}_{4}^{+}\). (b) Nitric acid, \(\mathrm{HNO}_{3}\), is a stronger acid than nitrous acid, \(\mathrm{HNO}_{2}\). (c) Ethanol and water have approximately the same acidity. (d) Trifluoroacetic acid, \(\mathrm{CF}_{3} \mathrm{COOH}\), is a stronger acid than trichloroacetic acid, \(\mathrm{CCl}_{g} \mathrm{COOH}\).

For each conjugate acid-base pair, identify the first species as an acid or base and the second species as its conjugate acid or conjugate base. In addition, draw Lewis structures for each species, showing all valence electrons and any formal charges. (a) \(\mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{HSO}_{4}{ }^{-}\) (b) \(\mathrm{NH}_{3}, \mathrm{NH}_{2}{ }^{-}\) (c) \(\mathrm{CH}_{3} \mathrm{OH}, \mathrm{CH}_{3} \mathrm{O}^{-}\)
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