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

Acids and Bases

Organic Chemistry

3. Acids and Bases

Acids and Bases

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4:54 minutes

Problem 52a,b

Textbook Question

What products are formed when each of the following reacts with HO⁻?
a. CH₃OH
b. ⁺NH₄

Verified step by step guidance

Step 1: Analyze the reaction of CH3OH (methanol) with HO− (hydroxide ion). Methanol is a weak acid, and hydroxide ion is a strong base. The hydroxide ion can deprotonate the hydroxyl group (-OH) of methanol, forming methoxide ion (CH3O−) and water (H2O). Write the reaction as: CH3OH + HO− → CH3O− + H2O.

Step 2: Consider the reaction of +NH4 (ammonium ion) with HO−. The ammonium ion is a weak acid, and hydroxide ion is a strong base. The hydroxide ion can deprotonate the ammonium ion, forming ammonia (NH3) and water (H2O). Write the reaction as: +NH4 + HO− → NH3 + H2O.

Step 3: For both reactions, identify the acid-base pairs. In the first reaction, CH3OH is the acid, and CH3O− is its conjugate base. In the second reaction, +NH4 is the acid, and NH3 is its conjugate base.

Step 4: Confirm that the reactions proceed in the direction that favors the formation of the weaker acid and base. In both cases, the products (CH3O− and NH3) are weaker bases compared to the reactants (HO−), and the reactions are thermodynamically favorable.

Step 5: Summarize the products formed. For part (a), the products are CH3O− and H2O. For part (b), the products are NH3 and H2O. Ensure the reactions are balanced and consistent with acid-base chemistry principles.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile, such as hydroxide ion (HO−), attacks a carbon atom, replacing a leaving group. In the case of CH3OH (methanol), the hydroxide ion can replace the hydroxyl group, leading to the formation of methoxide ion (CH3O−). Understanding this mechanism is crucial for predicting the products of reactions involving nucleophiles.

Ammonium Ion Reactivity

The ammonium ion (NH4+) is a positively charged species that can participate in acid-base reactions. When it reacts with HO−, it can undergo deprotonation, resulting in the formation of ammonia (NH3) and water. Recognizing the behavior of ammonium ions in the presence of strong bases is essential for predicting the outcome of such reactions.

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between species. In this context, HO− acts as a strong base, capable of accepting protons from acids like NH4+. Understanding the principles of acid-base chemistry helps in predicting the products formed when different organic compounds interact with hydroxide ions.

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Related Practice

Textbook Question

Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.

(c)

Textbook Question

In the following acid–base reactions,

1. draw Lewis structures of the reactants and the products.

2. determine which species are acting as electrophiles (acids) and which are acting as nucleophiles (bases).

3. use the curved-arrow formalism to show the movement of electron pairs in these reactions, as well as the imaginary movement in the resonance hybrids of the products.

4. indicate which reactions are best termed Brønsted–Lowry acid–base reactions.

(a)

Textbook Question

The following compounds can all react as acids.

a. For each compound, show its conjugate base. Show any resonance forms if applicable. b. Rank the conjugate bases in the order you would predict, from most stable to least stable.

Textbook Question

Ammonia appears in [TABLE 2-2 ] as both an acid and a conjugate base. a. Explain how ammonia can act as both an acid and a base. Which of these roles does it commonly fill in aqueous solutions?

b. Show how water can serve as both an acid and a base.

Textbook Question

Draw the products of the following reactions. Use curved arrows to show where the pair of electrons starts and where it ends up.

Textbook Question

What products are formed when each of the following reacts with HO⁻?

e. ⁺CH₃

f. FeBr₃

Textbook Question

a. Without using a calculator, estimate the pH of each of the following solutions:

1. [HO⁻] = 3.2 × 10⁻⁵

2. [H₃O⁺] = 8.3 × 10⁻¹

3. [H₃O⁺] = 1.7 × 10⁻³