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

Previous problemNext problem

5:03 minutes

Problem 1a

Textbook Question

Which of the following reactions favor formation of the products? Recall that the equilibrium favors formation of the weaker acid.

Verified step by step guidance

Step 1: Identify the acids and bases in each reaction. In the first reaction, CH3MgBr acts as a base and H2O acts as an acid. In the second reaction, CH3MgBr acts as a base and CH3OH acts as an acid.

Step 2: Recall the principle that equilibrium favors the formation of the weaker acid. To determine which side of the reaction is favored, compare the pKa values of the acids on both sides of the equilibrium. For the first reaction, compare the pKa of H2O and CH4. For the second reaction, compare the pKa of CH3OH and CH4.

Step 3: Use the pKa values from Appendix I. The pKa of H2O is approximately 15.7, the pKa of CH3OH is approximately 15.5, and the pKa of CH4 is approximately 50. Since CH4 has a much higher pKa, it is the weaker acid in both reactions.

Step 4: Analyze the equilibrium direction. In both reactions, the equilibrium will favor the side that forms CH4 because it is the weaker acid compared to H2O and CH3OH.

Step 5: Conclude that both reactions favor the formation of the products, as the equilibrium shifts toward the side with the weaker acid (CH4).

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Acid-Base Equilibrium

Acid-base equilibrium refers to the balance between acids and bases in a chemical reaction. In this context, the equilibrium favors the formation of the weaker acid and the stronger base. Understanding this concept is crucial for predicting the direction of the reaction and the stability of the products formed.

pKa Values

pKa values indicate the strength of an acid; lower pKa values correspond to stronger acids. In the context of the question, comparing the pKa values of the acids involved helps determine which reaction will favor product formation. The reaction will favor the side with the weaker acid, which is essential for analyzing the given reactions.

Grignard Reagents

Grignard reagents, such as CH3MgBr, are highly reactive organomagnesium compounds that act as nucleophiles in organic reactions. They can react with protic solvents like water and alcohols, leading to the formation of hydrocarbons and magnesium salts. Understanding their reactivity is key to predicting the outcomes of the reactions presented in the question.

Watch next

Master The 3 steps for determining the direction of acid and base equilibrium. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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.

(e) (CH₃)₃C–O^– + 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.

(d)

Textbook Question

Would amide or acetate most easily deprotonate an alcohol to make the alkoxide anion? Calculate K_eq for each possibility.

Textbook Question

Which of the following reactions favor formation of the products? Recall that the equilibrium favors formation of the weaker acid.

Textbook Question

The acid-catalyzed hydrolysis of an ester results in the formation of an equal amount of carboxylic acid and alcohol.

(a) Design a flow chart for separating the two products.

Textbook Question

Complete the following proposed acid–base reactions, and predict whether the reactants or products are favored.

(a)

(b)

Textbook Question

Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline

Textbook Question

Phenols are less acidic than carboxylic acids, with values of pK_a around 10. Phenols are deprotonated by (and therefore soluble in) solutions of sodium hydroxide but not by solutions of sodium bicarbonate. Explain how you would use extractions to isolate the three pure compounds from a mixture of p-cresol (p-methylphenol), cyclohexanone, and benzoic acid.

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap