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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1:12 minutes

Problem 66d

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)

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Identify the functional groups in the molecule. The given molecule contains an amine group (-NH2), a ketone group (C=O), and another amine group (-NH2) attached to the cyclohexane ring.

Determine the reactivity of each functional group with a strong base. Amines are basic and can act as nucleophiles, while the ketone group can undergo deprotonation at the alpha-carbon (the carbon adjacent to the carbonyl group) due to the acidity of the alpha-hydrogen.

Focus on the alpha-carbon of the ketone group. A strong base will abstract the alpha-hydrogen, forming an enolate ion. This is because the alpha-hydrogen is acidic due to resonance stabilization of the enolate ion.

Write the resonance structures of the enolate ion formed. The negative charge on the alpha-carbon can delocalize onto the oxygen atom of the carbonyl group, stabilizing the enolate ion.

Consider the overall product. The reaction with a single equivalent of a strong base will result in the formation of the enolate ion, which is the deprotonated form of the molecule at the alpha-carbon.

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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 reactions, they can facilitate nucleophilic attacks or promote elimination reactions. Understanding the strength and reactivity of the base is crucial for predicting the outcome of reactions involving functional groups like amines and carbonyls.

Amine Reactivity

Amines are basic due to the presence of a lone pair of electrons on the nitrogen atom, which can accept protons. When reacting with strong bases, amines can undergo deprotonation, leading to the formation of an anionic species. This property is essential for predicting how amines will behave in the presence of strong bases, especially in the context of forming new bonds or rearranging structures.

Carbonyl Compounds and Nucleophilicity

Carbonyl compounds, such as ketones and aldehydes, are electrophilic due to the partial positive charge on the carbon atom. They can react with nucleophiles, including deprotonated amines, to form new products. Understanding the reactivity of carbonyls is vital for predicting the products of reactions involving strong bases and amines, as they can lead to the formation of imines or other derivatives.

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Related Practice

Textbook Question

What is the conjugate acid of each of the following bases? [The most basic atom is indicated.]

(a)

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.

(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.

(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)

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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.(d)

Key Concepts

Strong Bases in Organic Chemistry

Amine Reactivity

Carbonyl Compounds and Nucleophilicity

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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.
(d)