Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
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Chapter 2, Problem 2.44P

What is K a for each compound? Use a calculator when necessary.

a. H 2 S p K a = 7.0

b. ClCH 2 COOH p K a = 2.8

c. HCN p K a = 9.1

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The value of Ka for H2S 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 2.44P

The value of Ka for H2S is 107.

Explanation of Solution

The given value of pKa is 7.0.

The value of Ka is calculated by the formula,

Ka=10pKa

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

Ka=10(7)Ka=107

Hence, the value of Ka is 107.

Conclusion

The value of Ka for H2S is 107.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The value of Ka for ClCH2COOH 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

pKa=[H3O+][A][HA]

pKa=logKa

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

Answer to Problem 2.44P

The value of Ka for ClCH2COOH is 1.585×103.

Explanation of Solution

The given value of pKa is 2.8.

The value of Ka is calculated by the formula,

Ka=10pKa

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

Ka=10(2.8)Ka=0.001585Ka=1.585×103

Hence, the value of Ka is 1.585×103.

Conclusion

The value of Ka for ClCH2COOH is 1.585×103.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The value of Ka for HCN 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 2.44P

The value of Ka for HCN is 7.943×1010.

Explanation of Solution

The given value of pKa is 9.1.

The value of Ka is calculated by the formula,

Ka=10pKa

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

Ka=10(9.1)Ka=8×1010

Hence, the value of Ka is 8×1010.

Conclusion

The value of Ka for HCN is 8×1010.

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Chapter 2 Solutions

Organic Chemistry

Ch. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.12PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - which compound in each pair of isomers is the...Ch. 2 - Prob. 2.15PCh. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - whichcompound in each pair is the stronger acid? a...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 - Prob. 2.25PCh. 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. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - a Draw the conjugate acid of ethylene, CH2 = CH2....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Prob. 2.40PCh. 2 - Draw the product of acid-base reaction. a. c. b....Ch. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 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 product of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - Rank the following ions in order of increasing...Ch. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - The pKa of three CH 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 - Prob. 2.58PCh. 2 - Ethyl butanoate, CH3CH2CH2CO2CH2CH3, is one of the...Ch. 2 - Prob. 2.60PCh. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Prob. 2.64PCh. 2 - Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - Prob. 2.70PCh. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Two pKa values are reported for malonic acid, a...Ch. 2 - Prob. 2.74PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.76PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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