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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1:14 minutes

Problem 66c

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)

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Identify the functional groups in the molecule. The structure contains a hydroxyl group (-OH) on the left side and a carboxylic acid group (-COOH) on the right side.

Determine the reactivity of the functional groups with a strong base. A strong base will deprotonate the most acidic hydrogen in the molecule. The carboxylic acid group is more acidic than the hydroxyl group due to resonance stabilization of the carboxylate anion.

Predict the site of deprotonation. The hydrogen attached to the oxygen in the carboxylic acid group will be removed by the strong base, forming a carboxylate anion (R-COO⁻).

Write the resulting structure after deprotonation. Replace the hydrogen in the carboxylic acid group with a negative charge on the oxygen atom, indicating the formation of the carboxylate anion.

Consider the stability of the product. The carboxylate anion is stabilized by resonance, making it the favored product of the reaction with a strong base.

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Key Concepts

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

Strong Bases in Organic Chemistry

Strong bases, such as sodium hydroxide (NaOH) or potassium tert-butoxide (KOtBu), are capable of deprotonating weak acids. In organic chemistry, they are often used to initiate reactions by removing protons from functional groups, such as alcohols or carboxylic acids, leading to the formation of alkoxides or carboxylate ions.

Deprotonation of Alcohols

Alcohols contain hydroxyl (-OH) groups that can act as weak acids. When a strong base is introduced, it can deprotonate the alcohol, resulting in the formation of an alkoxide ion. This process is crucial in many organic reactions, as the alkoxide can act as a nucleophile in subsequent steps.

Reaction Mechanisms

Understanding reaction mechanisms is essential for predicting the products of chemical reactions. In this case, the mechanism involves the deprotonation of hydroxyl groups by a strong base, leading to the formation of reactive intermediates that can further react with other molecules, ultimately determining the final product of the reaction.

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Related Practice

Textbook Question

What is the conjugate base of each of the following acids? [The most acidic proton is indicated.]

(d)

Textbook Question

What is the conjugate base of each of the following acids? [The most acidic proton is indicated.]

(a)

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

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.

(b)

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)

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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.(c)

Key Concepts

Strong Bases in Organic Chemistry

Deprotonation of Alcohols

Reaction Mechanisms

Watch next

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