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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1:27 minutes

Problem 10a

Textbook Question

Draw the product formed when pyridine reacts with ethyl bromide

Verified step by step guidance

Identify the functional groups and reactivity of the reactants: Pyridine is an aromatic heterocyclic compound with a nitrogen atom in the ring, and ethyl bromide is an alkyl halide (R-Br). The nitrogen in pyridine has a lone pair of electrons, making it a nucleophile.

Recognize the type of reaction: This is a nucleophilic substitution reaction (SN2 mechanism) because the nitrogen in pyridine will attack the electrophilic carbon in ethyl bromide, displacing the bromide ion (Br⁻).

Determine the site of attack: The lone pair on the nitrogen atom in pyridine will attack the carbon atom bonded to the bromine in ethyl bromide. This forms a bond between the nitrogen and the ethyl group.

Account for the charge: After the nitrogen in pyridine forms a bond with the ethyl group, it will carry a positive charge because it now has four bonds (quaternary ammonium ion).

Draw the product: The final product is an ethylpyridinium ion, where the ethyl group is attached to the nitrogen atom of pyridine, and the bromide ion (Br⁻) is the counterion.

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Key Concepts

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

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 case of pyridine reacting with ethyl bromide, the nitrogen atom in pyridine acts as a nucleophile, attacking the electrophilic carbon bonded to the bromine, leading to the formation of a new bond and the release of bromide ion.

Pyridine Structure and Reactivity

Pyridine is a six-membered aromatic heterocycle containing one nitrogen atom. Its aromatic nature and the presence of a lone pair on the nitrogen make it a weak base and a good nucleophile. Understanding the structure of pyridine is crucial, as it influences its reactivity in nucleophilic substitution reactions, particularly how it interacts with alkyl halides like ethyl bromide.

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (such as bromine). They are often used in nucleophilic substitution reactions due to the polar nature of the carbon-halogen bond, which makes the carbon susceptible to attack by nucleophiles. In this reaction, ethyl bromide serves as the alkyl halide that reacts with pyridine, facilitating the formation of a new product.

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