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

26. Amines

Amine Alkylation

Organic Chemistry

26. Amines

Amine Alkylation

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6:18 minutes

Problem 34d,e

Textbook Question

Within each structure, rank the indicated nitrogens by increasing basicity.
(d)
(e)

Verified step by step guidance

Step 1: Analyze the structures provided. In the first image (atabrine), the nitrogens labeled H and I are part of different environments. Nitrogen H is part of an amine group directly attached to an aromatic ring, while nitrogen I is part of a tertiary amine group. In the second image, the nitrogens labeled J, K, and L are part of different environments: J is part of an amide group, K is part of a secondary amine in a cyclic structure, and L is part of a secondary amine with a hydrogen attached.

Step 2: Recall the factors affecting basicity. Basicity is influenced by electron density on the nitrogen atom, resonance effects, inductive effects, and steric hindrance. Nitrogens with higher electron density and less resonance delocalization are generally more basic.

Step 3: For the first structure (atabrine), nitrogen H is less basic than nitrogen I because nitrogen H is attached to an aromatic ring, which delocalizes its lone pair through resonance, reducing its electron density. Nitrogen I, being part of a tertiary amine, has no resonance effects and is more basic due to higher electron density.

Step 4: For the second structure, nitrogen J is the least basic because it is part of an amide group, where the lone pair on nitrogen is delocalized into the carbonyl group, significantly reducing its electron density. Nitrogen K is more basic than J because it is part of a secondary amine in a cyclic structure, but it is less basic than nitrogen L due to steric hindrance and the cyclic environment. Nitrogen L is the most basic because it is a secondary amine with a hydrogen attached, allowing for higher electron density and minimal steric hindrance.

Step 5: Rank the nitrogens in each structure by increasing basicity. For the first structure: H < I. For the second structure: J < K < L.

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Key Concepts

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

Basicity of Nitrogen Compounds

Basicity refers to the ability of a nitrogen atom to accept protons (H+). In organic chemistry, the basicity of nitrogen is influenced by its hybridization, electronegativity, and the presence of electron-donating or withdrawing groups. Generally, sp3-hybridized nitrogens are more basic than sp2 or sp-hybridized ones due to the availability of lone pair electrons for protonation.

Inductive Effect

The inductive effect describes how the presence of electronegative atoms or groups can withdraw electron density from adjacent atoms, affecting their reactivity and basicity. Electron-withdrawing groups decrease basicity by stabilizing the lone pair on nitrogen, while electron-donating groups enhance basicity by increasing electron density around the nitrogen atom, making it more likely to accept protons.

Resonance Stabilization

Resonance stabilization occurs when a molecule can be represented by multiple valid Lewis structures, leading to delocalization of electrons. In nitrogen-containing compounds, resonance can significantly affect basicity; if the lone pair on nitrogen is involved in resonance with other atoms, it becomes less available for protonation, thus decreasing the basicity of that nitrogen.

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Within each structure, rank the indicated nitrogens by increasing basicity.(d) (e)

Key Concepts

Basicity of Nitrogen Compounds

Inductive Effect

Resonance Stabilization

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Within each structure, rank the indicated nitrogens by increasing basicity.
(d)
(e)