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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2:10 minutes

Problem 66b

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(b)

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Identify the functional groups in the molecule. The structure contains two carboxylic acid groups (-COOH) and a chlorine atom attached to the cyclohexane ring.

Determine the reactivity of the molecule with a strong base. Carboxylic acids are acidic and will react with a strong base to form their conjugate base, the carboxylate anion (-COO⁻). The chlorine atom may also influence the reactivity due to its electron-withdrawing nature.

Predict the reaction of the strong base with the carboxylic acid groups. A single equivalent of a strong base will deprotonate one of the carboxylic acid groups, forming a carboxylate anion and leaving the other carboxylic acid group intact.

Consider the position of the chlorine atom. The chlorine atom is electron-withdrawing and may stabilize the carboxylate anion formed near it, making the carboxylic acid group closer to the chlorine more likely to be deprotonated.

Write the expected product. The molecule will have one carboxylic acid group converted to a carboxylate anion (-COO⁻), while the other carboxylic acid group remains unchanged. The chlorine atom remains attached to the cyclohexane ring.

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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, strong bases can deprotonate acidic functional groups, such as alcohols or carboxylic acids, leading to the formation of alkoxide ions or carboxylate ions. Understanding the acidity of functional groups is crucial for predicting the products of these reactions.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the provided molecule, the chlorine atom is a good leaving group, and when a strong base is present, it can facilitate the substitution reaction, leading to the formation of new products.

Functional Group Reactivity

Different functional groups exhibit varying reactivities based on their electronic properties. In the given molecule, the presence of hydroxyl (-OH) and carbonyl (C=O) groups influences how the molecule interacts with a strong base. Recognizing the reactivity of these groups is essential for predicting the outcome of the reaction and the stability of the resulting products.

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Related Practice

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(e)

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(d)

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(c)

Textbook Question

Provide an arrow-pushing mechanism for the following acid–base reactions.

(d)

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(a)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(c)

Textbook Question

In the following reactions,

(i) identify the acid and base,

(ii) identify the most electron-rich atom in the base,

(iii) identify the most acidic hydrogen in the acid,

(c)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(b)

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For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.(b)

Key Concepts

Acid-Base Reactions

Nucleophilic Substitution

Functional Group Reactivity

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For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(b)