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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3:13 minutes

Problem 42c,d

Textbook Question

Predict the products of the following acid–base reactions.
(c)
(d)

Verified step by step guidance

Step 1: Identify the acid and base in each reaction. In reaction (c), the acid is benzoic acid (C₆H₅COOH) and the base is hydroxide ion (OH⁻). In reaction (d), the acid is carbonic acid (HOCOOH) and the base is hydroxide ion (OH⁻).

Step 2: Understand the acid-base reaction mechanism. The hydroxide ion (OH⁻) will deprotonate the acidic hydrogen from the carboxylic acid group (COOH) in both reactions.

Step 3: Predict the products for reaction (c). When benzoic acid (C₆H₅COOH) reacts with hydroxide ion (OH⁻), the product will be the benzoate ion (C₆H₅COO⁻) and water (H₂O).

Step 4: Predict the products for reaction (d). Carbonic acid (HOCOOH) will react with two hydroxide ions (OH⁻) to form carbonate ion (CO₃²⁻) and water (H₂O).

Step 5: Write the balanced chemical equations for each reaction. For reaction (c), C₆H₅COOH + OH⁻ ⇌ C₆H₅COO⁻ + H₂O. For reaction (d), HOCOOH + 2 OH⁻ ⇌ CO₃²⁻ + 2 H₂O.

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Key Concepts

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

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In organic chemistry, acids are proton donors, while bases are proton acceptors. Understanding the strength of acids and bases, as well as their conjugate pairs, is crucial for predicting the products of these reactions.

Equilibrium in Reactions

Many acid-base reactions are reversible and can reach a state of equilibrium, where the rate of the forward reaction equals the rate of the reverse reaction. The position of equilibrium can be influenced by factors such as concentration, temperature, and the nature of the reactants, which is essential for predicting the predominant products.

Resonance Structures

Resonance structures are different ways of drawing a molecule that represent the same compound. In the context of acid-base reactions, resonance can stabilize charged species, influencing their reactivity. Recognizing resonance can help predict the stability of intermediates and the overall direction of the reaction.

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Related Practice

Textbook Question

Consider the following reaction:

HBr + ^-C≡N ⇌ Br⁻+ HC≡N

c. What is the conjugate base of the acid on the left?

d. What is the conjugate acid of the base on the left?

Textbook Question

Draw the conjugate acid of each of the following:

a. CH₃CH₂OH

b. CH₃CH₂O⁻

Textbook Question

What is the conjugate acid of each of the following?

1. NH₃

2. Cl⁻

3. HO⁻

4. H₂O

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.

(b)

Textbook Question

Predict the products of the following acid–base reactions.

(a) H₂SO₄ + CH₃COO^– ⇌

(b) CH₃COOH + (CH₃)₃N: ⇌

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.

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Predict the products of the following acid–base reactions. (c) (d)

Key Concepts

Acid-Base Reactions

Equilibrium in Reactions

Resonance Structures

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Predict the products of the following acid–base reactions.
(c)
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