Table of contents

1. Matter and Measurements4h 31m
2. Atoms and the Periodic Table5h 23m
3. Ionic Compounds2h 18m
4. Molecular Compounds2h 18m
5. Classification & Balancing of Chemical Reactions3h 17m
6. Chemical Reactions & Quantities2h 27m
7. Energy, Rate and Equilibrium3h 46m
8. Gases, Liquids and Solids3h 25m
9. Solutions4h 10m
10. Acids and Bases3h 29m
11. Nuclear Chemistry56m
BONUS: Lab Techniques and Procedures1h 38m
BONUS: Mathematical Operations and Functions47m
12. Introduction to Organic Chemistry1h 34m
13. Alkenes, Alkynes, and Aromatic Compounds2h 12m
14. Compounds with Oxygen or Sulfur1h 6m
15. Aldehydes and Ketones1h 1m
16. Carboxylic Acids and Their Derivatives1h 11m
17. Amines39m
18. Amino Acids and Proteins1h 51m
19. Enzymes1h 37m
20. Carbohydrates1h 41m
21. The Generation of Biochemical Energy2h 8m
22. Carbohydrate Metabolism2h 22m
23. Lipids2h 26m
24. Lipid Metabolism1h 45m
25. Protein and Amino Acid Metabolism1h 37m
26. Nucleic Acids and Protein Synthesis2h 54m

17. Amines

Classifying Amines

GOB Chemistry

17. Amines

Classifying Amines

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Problem 49

Textbook Question

Which is the stronger base, trimethylamine or ammonia? In which direction will the following reaction proceed?

Verified step by step guidance

Step 1: Understand the concept of base strength. A stronger base is better at accepting protons (H⁺). The strength of a base is influenced by factors such as the availability of the lone pair of electrons on the nitrogen atom and the surrounding molecular structure.

Step 2: Compare the structures of trimethylamine (N(CH₃)₃) and ammonia (NH₃). Trimethylamine has three methyl groups attached to the nitrogen atom, while ammonia has only hydrogen atoms attached to the nitrogen.

Step 3: Analyze the electron-donating effect of the methyl groups in trimethylamine. Methyl groups are electron-donating, which increases the electron density on the nitrogen atom, making it more available to accept a proton. This suggests that trimethylamine is a stronger base than ammonia.

Step 4: Consider the reaction direction. In a reaction involving a stronger base and a weaker base, the equilibrium will favor the formation of the weaker base because the stronger base will more readily accept a proton. Identify the bases and acids on both sides of the reaction to determine the direction.

Step 5: Use the concept of equilibrium to predict the reaction direction. If trimethylamine is the stronger base, the reaction will proceed in the direction that forms ammonia (the weaker base) and its conjugate acid. Verify this by analyzing the acid-base pairs in the reaction.

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Key Concepts

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

Brønsted-Lowry Theory of Acids and Bases

The Brønsted-Lowry theory defines acids as proton donors and bases as proton acceptors. This framework helps in understanding the strength of bases by evaluating their ability to accept protons. In this context, comparing trimethylamine and ammonia involves analyzing their respective tendencies to accept protons from acids.

Base Strength

Base strength refers to the ability of a substance to accept protons. In general, stronger bases have a higher tendency to attract protons compared to weaker bases. Trimethylamine, with its three methyl groups, is more sterically hindered than ammonia, which can influence its basicity and the direction of the reaction.

Equilibrium and Reaction Direction

In chemical reactions, the direction in which a reaction proceeds is determined by the relative strengths of the acids and bases involved. The reaction will favor the formation of the weaker acid and weaker base. Understanding the equilibrium concept is crucial for predicting whether trimethylamine or ammonia will act as the stronger base in a given reaction.

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Textbook Question

Classify each of the following amines as primary (1°), secondary (2°), or tertiary (3°):

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Textbook Question

Classify each of the following amines as primary (1°), secondary (2°), or tertiary (3°):

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Textbook Question

Classify each of the following amines as primary (1°), secondary (2°), or tertiary (3°):

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Textbook Question

Draw the condensed and line formula of the molecule in the margin. Is it a primary, secondary, or tertiary amine? Why?

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Textbook Question

Draw the structure of the following amino acids, dipeptides, and tripeptides at low pH (pH 1) and high pH (pH 14). At each pH, assume that all functional groups that might do so are ionized.

e. Gln-Ala-Asn

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Textbook Question

Which of the following compounds are heterocyclic nitrogen compounds?

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Textbook Question

Draw the structures of (a) ethylamine and (b) trimethylamine. Use dashed lines to show how they would form hydrogen bonds to water molecules.

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Textbook Question

Which is the stronger base in each pair?

a. Ammonia or ethylamine