ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
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Chapter 2, Problem 2.49P

Draw the products of each reaction. Use the p K a table in Appendix A to decide if the equilibrium favors the starting materials or products.

a. CH 3 NH 2 + H 2 SO 4

b. Chapter 2, Problem 2.49P, Draw the products of each reaction. Use the pKa table in Appendix A to decide if the equilibrium , example  1

c. Chapter 2, Problem 2.49P, Draw the products of each reaction. Use the pKa table in Appendix A to decide if the equilibrium , example  2

d. H C C H + CH 3 CH 2 Li +

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The products of the given reaction are to be drawn. If the equilibrium favors the starting materials or a product is to be predicted.

Concept introduction: According to Bronsted-Lowry theory, when an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid.

In a reaction which strongly favors the formation of products, the base used to remove proton from the acid should be stronger than the base formed when the proton is removed. In a reaction which favors the products, equilibrium will favors the formation of the weaker acid or weaker base. The pKa value of the products is higher than the pKa value of the reactants.

Answer to Problem 2.49P

The products of the given reaction are CH3NH3+ and HSO4. The equilibrium favors the product formation.

Explanation of Solution

The complete reaction between methyl amine and H2SO4 is shown below.

CH3NH2+H2SO4CH3NH3+ + HSO4   Base       Acid         Conjugate    Conjugate                                     acid                base

The pKa value of H2SO4 is 9 and the pKa value of CH3NH3+ is 10.7. The equilibrium favors the formation of a weaker acid with a higher pKa value. The pKa value of an acid is lower than the pKa value of a conjugate acid. Hence, equilibrium favors the product formation.

Conclusion

The products of the given reaction are CH3NH3+ and HSO4. The equilibrium favors the product formation.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The products of the given reaction are to be drawn. If the equilibrium favors the starting materials or a product is to be predicted.

Concept introduction: According to Bronsted-Lowry theory, when an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid.

In a reaction which strongly favors the formation of products, the base used to remove proton from the acid should be stronger than the base formed when the proton is removed. In a reaction which favors the products, equilibrium will favors the formation of the weaker acid or weaker base. The pKa value of the products is higher than the pKa value of the reactants.

Answer to Problem 2.49P

The products of the given reaction are CH3CH2COONa and HCl. The equilibrium favors the starting materials.

Explanation of Solution

The complete reaction between propanoic acid and sodium chloride is shown below.

NaCl+CH3CH2COOHHCl +CH3CH2COONa   Base       Acid               Conjugate     Conjugate                                           acid                base

The pKa value of propanoic acid is 4.9 and the pKa value of HCl is 7. The equilibrium favors the formation of a weaker acid with a higher pKa value. The pKa value of an acid is greater than the pKa value of a conjugate acid. Hence, equilibrium favors the starting materials.

Conclusion

The products of the given reaction are CH3CH2COONa and HCl. The equilibrium favors the starting materials.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The products of the given reaction are to be drawn. If the equilibrium favors the starting materials or a product is to be predicted.

Concept introduction: According to Bronsted-Lowry theory, when an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid.

In a reaction which strongly favors the formation of products, the base used to remove proton from the acid should be stronger than the base formed when the proton is removed. In a reaction which favors the products, equilibrium will favors the formation of the weaker acid or weaker base. Or the pKa value of the products is higher than the pKa value of the reactants.

Answer to Problem 2.49P

The products of the given reaction are H2CO3 and C6H5ONa . The equilibrium favors the starting materials.

Explanation of Solution

The complete reaction between phenol and sodium hydrogen carbonate is shown below.

NaHCO3+C6H5OHH2CO3 +       C6H5ONa   Base       Acid               Conjugate     Conjugate                                           acid                base

The pKa value of phenol is 10 and the pKa value of H2CO3 is 6.4. The equilibrium favors the formation of a weaker acid with a higher pKa value. The pKa value of an acid is greater than the pKa value of a conjugate acid. Hence, equilibrium favors the starting materials.

Conclusion

The products of the given reaction are H2CO3 and C6H5ONa . The equilibrium favors the starting materials.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The products of the given reaction are to be drawn. If the equilibrium favors the starting materials or a product is to be predicted.

Concept introduction: According to Bronsted-Lowry theory, when an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid.

In a reaction which strongly favors the formation of products, the base used to remove proton from the acid should be stronger than the base formed when the proton is removed. In a reaction which favors the products, equilibrium will favors the formation of the weaker acid or weaker base. Or the pKa value of the products is higher than the pKa value of the reactants.

Answer to Problem 2.49P

The products of the given reaction are CH3CH3 and HCCLi. The equilibrium favors the product formation.

Explanation of Solution

The complete reaction between ethyne and ethyl lithium is shown below.

CH3CH2Li+HCCHCH3CH3+ HCCLi   Base                  Acid               Conjugate    Conjugate                                                     acid                base

The pKa value of ethyne is 25 and the pKa value of CH3CH3 is 50. The equilibrium favors the formation of a weaker acid with a higher pKa value. The pKa value of an acid is lower than the pKa value of a conjugate acid. Hence, equilibrium favors the product formation.

Conclusion

The products of the given reaction are CH3CH3 and HCCLi. The equilibrium favors the product formation.

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Chapter 2 Solutions

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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