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

Reductive Amination

Organic Chemistry

26. Amines

Reductive Amination

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2:19 minutes

Problem 40f

Textbook Question

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(f)

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Step 1: Begin with m-toluidine, which has an amino group (-NH2) and a methyl group (-CH3) attached to a benzene ring in the meta position. The goal is to convert the amino group into an N-cyclopentyl group.

Step 2: Perform an alkylation reaction on the amino group. Use cyclopentyl bromide (C5H9Br) or cyclopentyl chloride (C5H9Cl) as the alkylating agent. This reaction typically requires a base, such as potassium carbonate (K2CO3), to neutralize the acid formed during the reaction.

Step 3: The reaction mechanism involves the nucleophilic attack of the lone pair on the nitrogen atom of the amino group (-NH2) on the electrophilic carbon of the cyclopentyl halide. This results in the formation of an N-cyclopentyl group attached to the nitrogen.

Step 4: Ensure the reaction conditions are mild to avoid over-alkylation or side reactions. The product formed will be N-cyclopentyl-m-toluidine, where the nitrogen is now bonded to the cyclopentyl group.

Step 5: Purify the product using techniques such as recrystallization or column chromatography to isolate N-cyclopentyl-m-toluidine in its pure form.

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Key Concepts

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

Amines and Their Reactivity

Amines, such as m-toluidine, are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. They are nucleophilic and can participate in various reactions, including electrophilic aromatic substitution and acylation. Understanding the reactivity of amines is crucial for predicting the products of their transformations.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. The presence of substituents, like the amino group in m-toluidine, influences the reactivity and orientation of the substitution. Recognizing how substituents direct EAS is essential for determining the products formed in the conversion of m-toluidine.

Functional Group Transformations

Functional group transformations involve converting one functional group into another through chemical reactions. In the context of m-toluidine, this may include oxidation, acylation, or alkylation processes. Mastery of these transformations is vital for synthesizing desired compounds from m-toluidine, as it allows chemists to manipulate the molecule's reactivity and properties effectively.

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Related Practice

Textbook Question

The two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides. Show how these techniques can be used to accomplish the following syntheses.

(b) benzaldehyde → benzylamine

Textbook Question

Propose mechanisms for the following reactions.

(a)

Textbook Question

Show how to synthesize the following amines from the indicated starting materials by reductive amination.

(a) benzylmethylamine from benzaldehyde

(b) N-benzylpiperidine from piperidine

Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

Textbook Question

Using any necessary reagents, show how you would accomplish the following syntheses.

(d)

Textbook Question

Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.

Textbook Question

Predict the products of the following reactions:

(h)

Textbook Question

Show how to synthesize the following amines from the indicated starting materials by reductive amination.

(e)

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Show how m-toluidine can be converted to the following compounds, using any necessary reagents.(f)

Key Concepts

Amines and Their Reactivity

Electrophilic Aromatic Substitution

Functional Group Transformations

Watch next

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(f)