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

Nitrogenous Nucleophiles

Organic Chemistry

26. Amines

Nitrogenous Nucleophiles

Previous problemNext problem

8:04 minutes

Problem 23c

Textbook Question

Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.
(c) piperidine

Verified step by step guidance

Understand the reaction: Sodium nitrite (NaNO₂) in dilute HCl generates nitrous acid (HNO₂) in situ. This reagent reacts with amines to form different products depending on the type of amine (primary, secondary, or tertiary). Piperidine is a secondary amine, so it will undergo nitrosation to form an N-nitrosoamine.

Write the structure of piperidine: Piperidine is a six-membered saturated heterocyclic ring containing one nitrogen atom. Its molecular formula is C₅H₁₁N, and the nitrogen atom has a lone pair of electrons, making it nucleophilic.

Describe the reaction mechanism: The lone pair on the nitrogen atom of piperidine attacks the nitrosonium ion (NO⁺), which is generated from the reaction of nitrous acid (HNO₂) with HCl. This leads to the formation of an N-nitrosoamine.

Draw the product: The product of the reaction is N-nitrosopiperidine, where the nitrogen atom in piperidine is bonded to a nitroso group (-NO). The structure of N-nitrosopiperidine can be represented as a six-membered ring with the nitrogen atom attached to the -NO group.

Verify the reaction conditions: Ensure that the reaction is carried out under acidic conditions (dilute HCl) and at a low temperature, as nitrosation reactions are typically sensitive to these parameters.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Amines

Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can be classified as primary, secondary, or tertiary based on the number of carbon-containing groups attached to the nitrogen atom. Understanding the structure and reactivity of amines is crucial for predicting their behavior in chemical reactions.

Diazotization

Diazotization is a chemical reaction that involves the conversion of primary amines into diazonium salts using sodium nitrite (NaNO2) in the presence of a strong acid, such as hydrochloric acid (HCl). This process is essential for synthesizing various aromatic compounds and is characterized by the formation of a stable diazonium ion, which can undergo further reactions to yield different products.

Piperidine Reactivity

Piperidine is a six-membered saturated heterocyclic amine with a nitrogen atom in the ring. Unlike primary amines, piperidine is a secondary amine, which influences its reactivity during diazotization. Understanding how piperidine interacts with sodium nitrite and HCl is key to predicting the products formed, as it may lead to different outcomes compared to simpler amines.

Watch next

Master Four Ways to Make a Primary Amine Precursor with a bite sized video explanation from Johnny

Start learning