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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5:04 minutes

Problem 67

Textbook Question

From which of the following compounds can HO⁻ remove a proton in a reaction that favors product formation?

Verified step by step guidance

Step 1: Understand the concept of acidity and basicity. Hydroxide ion (HO⁻) acts as a base and can remove a proton (H⁺) from a compound if the compound has an acidic proton. The reaction will favor product formation if the resulting conjugate base is more stable than the original base.

Step 2: Evaluate the acidity of the compounds provided. Look for factors that increase acidity, such as electronegativity of the atom bonded to the proton, resonance stabilization of the conjugate base, and inductive effects from electronegative groups.

Step 3: Compare the pKa values of the compounds. A lower pKa value indicates a stronger acid, meaning the compound is more likely to donate a proton to HO⁻. If the pKa of the compound is significantly lower than the pKa of water (15.7), the reaction is likely to favor product formation.

Step 4: Analyze the stability of the conjugate base formed after the proton is removed. Stability can be enhanced by resonance, inductive effects, or the presence of electronegative atoms. If the conjugate base is stable, the reaction will favor product formation.

Step 5: Determine which compound has the most acidic proton based on the above factors. The compound with the most acidic proton will be the one from which HO⁻ can remove a proton in a reaction that favors product formation.

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Key Concepts

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

Acidity and Basicity

Acidity refers to the tendency of a compound to donate protons (H+ ions), while basicity is the ability to accept protons. In organic chemistry, the strength of an acid is often measured by its pKa value; lower pKa values indicate stronger acids. Understanding the relative acidity of compounds is crucial for predicting which can be deprotonated by hydroxide ions (HO−) in a reaction.

Equilibrium and Reaction Favorability

Chemical reactions reach a state of equilibrium where the rate of the forward reaction equals the rate of the reverse reaction. The position of equilibrium is influenced by the stability of the products and reactants. A reaction favors product formation when the products are more stable than the reactants, often determined by factors such as bond strength and sterics.

Proton Transfer Reactions

Proton transfer reactions involve the transfer of a proton from an acid to a base. In the context of the question, HO− acts as a base that can remove a proton from an acidic compound. The ability of HO− to effectively remove a proton depends on the acidity of the compound in question and the stability of the resulting conjugate base.

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Related Practice

Textbook Question

The K_a of phenylacetic acid is 5.2 × 10⁻⁵, and the pK_a of propionic acid is 4.87.

c. Predict whether the following equilibrium will favor the reactants or the products.

Textbook Question

Write equations for the following acid–base reactions. Use the information in Table 2-2 or Appendix 4 to predict whether the equilibrium will favor the reactants or the products.

a. HCOOH + ^–CN

b. CH₃COO^– + CH₃OH

c. (CH₃)₂CHOH + NaNH₂

Textbook Question

For each of the following reactions, suggest which solvent(s) would be compatible with the acids and bases involved. (We will ignore any other possible reactions for now.) Your choices of solvents are pentane, diethyl ether, ethanol, water, and ammonia. Refer to Appendix 4 for any needed values of pK_a, or estimate them.

a. CH₃Li + H—C≡C—H → CH₄ + H—C≡CLi

b. CH₃Li + (CH₃)3C—OH → CH₄ + (CH₃)₃C—OLi

Textbook Question

For each of the following pairs of reactions, indicate which one has the more favorable equilibrium constant (that is, which one most favors products):

Textbook Question

How could you separate a mixture of the following compounds? The reagents available to you are water, ether, 1.0 M HCl, and 1.0 M NaOH.

Textbook Question

Which of the following bases can remove a proton from acetic acid in a reaction that favors products?

HO⁻ CH₃NH₂ HC≡C⁻ CH₃OH H₂O Cl⁻

Textbook Question

Give the products of the following acid–base reactions and indicate whether reactants or products are favored at equilibrium.

Textbook Question

Give the products of the following acid–base reactions and indicate whether reactants or products are favored at equilibrium.

b. CH₃CH₂OH + ^-NH₂ ⇌

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From which of the following compounds can HO− remove a proton in a reaction that favors product formation?

Key Concepts

Acidity and Basicity

Equilibrium and Reaction Favorability

Proton Transfer Reactions

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From which of the following compounds can HO⁻ remove a proton in a reaction that favors product formation?