Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

3. Acids and Bases

Acid Base Equilibrium

Organic Chemistry

3. Acids and Bases

Acid Base Equilibrium

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3:12 minutes

Problem 13j

Textbook Question

Write equations for the following acid–base reactions. Label the conjugate acids and bases, and show any inductive stabilization. Predict whether the equilibrium favors the reactants or products. Try to do this without using a table of pKa values, but if you need a hint, you can consult Appendix 4.
j. CF₃CH₂O^– + FCH₂CH₂OH

Verified step by step guidance

Identify the acid and base in the reaction. In this case, CF3CH2O- is the base and FCH2CH2OH is the acid. The base will accept a proton from the acid.

Write the chemical equation for the acid-base reaction:

{CF 3 CH 2 O}_{-} + F CH 2 CH 2 OH \to CF 3 CH 2 OH + {F CH 2 CH 2 O}_{-}

Label the conjugate acid and base. After the reaction, CF3CH2OH is the conjugate acid and FCH2CH2O- is the conjugate base.

Consider inductive effects for stabilization. The CF3 group is highly electronegative and can stabilize the negative charge on CF3CH2O- through inductive effects, making it a weaker base compared to FCH2CH2O-. This suggests that the equilibrium may favor the formation of CF3CH2OH and FCH2CH2O-.

Predict the direction of equilibrium. Without using pKa values, consider the stability of the conjugate base and acid. The inductive effect of the CF3 group suggests that the equilibrium will favor the products, as CF3CH2OH is a weaker acid compared to FCH2CH2OH.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acid-Base Reaction Mechanism

Acid-base reactions involve the transfer of protons (H+) between molecules. The acid donates a proton, becoming its conjugate base, while the base accepts a proton, forming its conjugate acid. Understanding the mechanism helps in identifying the reactants and products in the reaction, as well as labeling the conjugate acids and bases.

Inductive Effect

The inductive effect refers to the electron-withdrawing or electron-donating influence exerted by substituents through sigma bonds. In organic chemistry, electronegative groups like CF3 can stabilize or destabilize ions by affecting electron density, which can influence the acidity or basicity of molecules and the direction of equilibrium in acid-base reactions.

Equilibrium Prediction in Acid-Base Reactions

Predicting the direction of equilibrium in acid-base reactions involves assessing the relative stability of reactants and products. Factors such as inductive effects and resonance stabilization play a role. Generally, equilibrium favors the side with the more stable conjugate acid-base pair, which can be inferred without pKa values by considering molecular structure and stabilization effects.

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Related Practice

Textbook Question

For each of the acid–base reactions in [Section 2.3], compare the pK_a values of the acids on either side of the equilibrium arrows to prove that the equilibrium lies in the direction indicated.

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Textbook Question

For each of the acid–base reactions in [Section 2.3], compare the pK_avalues of the acids on either side of the equilibrium arrows to prove that the equilibrium lies in the direction indicated.

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Textbook Question

Ethyne (HC≡CH) has a pK_a value of 25, water has a pK_a value of 15.7, and ammonia (NH3) has a pKa value of 36. Draw the equation, showing equilibrium arrows that indicate whether reactants or products are favored, for the acid–base reaction of ethyne with

a. HO^-.

Textbook Question

Given the data in Problem 47:

a. What pH would you make the water layer to cause the carboxylic acid to dissolve in the water layer and the amine to dissolve in the ether layer?

Textbook Question

Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

(g) KOH + CH₃CH₂OH ⇌

Textbook Question

Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

(f) (CH₃)₃C–O^– + H₂O ⇌

Textbook Question

Write equations for the following acid–base reactions. Label the conjugate acids and bases, and show any inductive stabilization. Predict whether the equilibrium favors the reactants or products. Try to do this without using a table of pK_a values, but if you need a hint, you can consult Appendix 4.

g. NaOCH₂CH₃ + Cl₂CHCH₂OH

h. H₂Se + NaNH₂

i. CH₃CHFCOOH + FCH₂CH₂COO^–

Textbook Question

For each of the following compounds (here shown in their acidic forms), write the form that predominates in a solution with a pH = 5.5:

c. H₃O⁺ (pK_a = −1.7)

d. HBr (pK_a = −9)

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