PKG ORGANIC CHEMISTRY
PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
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Textbook Question
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Chapter 2, Problem 2.46P

What is the p K a for each compound?

a. Chapter 2, Problem 2.46P, What is the pKa for each compound? a. b. c. , example  1

b. Chapter 2, Problem 2.46P, What is the pKa for each compound? a. b. c. , example  2

c. Chapter 2, Problem 2.46P, What is the pKa for each compound? a. b. c. , example  3

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The value of pKa for the given compound is to be calculated.

Concept introduction: The equilibrium constant of an acid dissociation reaction depends on the strength of an acid involved in the reaction. The Ka value is large for strong acids and small for weak acids.

Acid dissociation constant Ka represents the acidity of an acid in a solution.

For an acid dissociation reaction,

HA+H2OH3O++A

Ka=[H3O+][A][HA]

pKa=logKa

The strength of an acid decreases as the value of pKa increases.

Answer to Problem 2.46P

The value of pKa for the given compound is 9.3279.

Explanation of Solution

The given value of Ka is 4.7×1010.

The value of pKa is calculated by the formula,

pKa=logKa

Substitute the value of Ka in the above formula to calculate the value of pKa.

pKa=log(4.7×1010)=[log(4.7)+log1010]=log(4.7)+10=0.6721+10

Simplify the above equation,

pKa=9.3279

Hence, the value of pKa for the given compound is 9.3279.

Conclusion

The value of pKa for the given compound is 9.3279.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The value of pKa for the given compound is to be calculated.

Concept introduction: The equilibrium constant of an acid dissociation reaction depends on the strength of an acid involved in the reaction. The Ka value is large for strong acids and small for weak acids.

Acid dissociation constant Ka represents the acidity of an acid in a solution.

For an acid dissociation reaction,

HA+H2OH3O++A

Ka=[H3O+][A][HA]

pKa=logKa

The strength of an acid decreases as the value of pKa increases.

Answer to Problem 2.46P

The value of pKa for the given compound is 4.6383.

Explanation of Solution

The given value of Ka is 2.3×105.

The value of pKa is calculated by the formula,

pKa=logKa

Substitute the value of Ka in the above formula to calculate the value of pKa.

pKa=log(2.3×105)=[log(2.3)+log105]=log(2.3)+5=0.3617+5

Simplify the above equation,

pKa=4.6383

Hence, the value of pKa for the given compound is 4.6383.

Conclusion

The value of pKa for the given compound is 4.6383.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The value of pKa for the given compound is to be calculated.

Concept introduction: The equilibrium constant of an acid dissociation reaction depends on the strength of an acid involved in the reaction. The Ka value is large for strong acids and small for weak acids.

Acid dissociation constant Ka represents the acidity of an acid in a solution.

For an acid dissociation reaction,

HA+H2OH3O++A

Ka=[H3O+][A][HA]

pKa=logKa

The strength of an acid decreases as the value of pKa increases.

Answer to Problem 2.46P

The value of pKa for the given compound is 0.23.

Explanation of Solution

The given value of Ka is 5.9×101.

The value of pKa is calculated by the formula,

pKa=logKa

Substitute the value of Ka in the above formula to calculate the value of pKa.

pKa=log(5.9×101)=[log(5.9)+log101]=log(5.9)+1=0.7709+1

Simplify the above equation.

pKa=0.23

Hence, the value of pKa for the given compound is 0.23.

Conclusion

The value of pKa for the given compound is 0.23.

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Chapter 2 Solutions

PKG ORGANIC CHEMISTRY

Ch. 2 - Prob. 2.11PCh. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.13PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - Rank the labeled H atoms in the following compound...Ch. 2 - Which hydrogen in each molecule is most...Ch. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - Which compound in each pair of isomers is the...Ch. 2 - Which compound in each pair is the stronger acid?...Ch. 2 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2 - Explain the apparent paradox. HBr is a stronger...Ch. 2 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2 - Acetonitrile (CH3CN) has a pKa of 25, making it...Ch. 2 - For each pair of compounds: [1] Which indicated H...Ch. 2 - Rank the compounds in each group in order of...Ch. 2 - Which proton in each of the following drugs is...Ch. 2 - Which anion A or B is the stronger base? ABCh. 2 - Prob. 2.28PCh. 2 - Problem 2.29 Compounds like amphetamine that...Ch. 2 - Problem 2.30 Which species are Lewis bases? a. b....Ch. 2 - Which species are Lewis acids? a. b. c. d. Ch. 2 - For each reaction, label the Lewis acid and base....Ch. 2 - Prob. 2.33PCh. 2 - Prob. 2.34PCh. 2 - Label the Lewis acid and base. Use curved arrow...Ch. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - 2.38 What is the conjugate acid of each base? a....Ch. 2 - 2.39 What is the conjugate base of each acid? a....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Prob. 2.43PCh. 2 - Prob. 2.44PCh. 2 - What is Ka for each compound? Use a calculator...Ch. 2 - What is the pKa for each compound? a. b. c.Ch. 2 - Which of the following bases are strong enough to...Ch. 2 - Which compounds can be deprotonated by OH, so that...Ch. 2 - Draw the products of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - 2.51 Rank the following ions in order of...Ch. 2 - Prob. 2.52PCh. 2 - Prob. 2.53PCh. 2 - 2.54 The of three bonds is given below. a. For...Ch. 2 - a. What is the conjugate acid of A? b. What is the...Ch. 2 - 2.56 Draw the structure of a constitutional isomer...Ch. 2 - 2.57 Many drugs are Bronsted-Lowry acids or...Ch. 2 - Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH)...Ch. 2 - 2.59 Atenolol is a (beta) blocker, a drug used to...Ch. 2 - 2.60 Use the principles in Section 2.5 to label...Ch. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.63 Classify each compound as a Lewis base, a...Ch. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Label the Lewis acid and Lewis base in each...Ch. 2 - 2.66 Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.67PCh. 2 - 2.68 Answer the following questions about the four...Ch. 2 - Prob. 2.69PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Prob. 2.74PCh. 2 - Prob. 2.75PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.77PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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