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

Amines by Reduction

Organic Chemistry

26. Amines

Amines by Reduction

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6:26 minutes

Problem 40b

Textbook Question

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

(b)

Verified step by step guidance

Step 1: Begin with m-toluidine (C6H4CH3NH2), which contains an amino group (-NH2) and a methyl group (-CH3) attached to a benzene ring in the meta position. Identify the target compound and determine the functional group transformations required.

Step 2: Protect the amino group (-NH2) to prevent unwanted reactions during subsequent steps. This can be achieved by acetylation using acetic anhydride (CH3CO)2O, forming an acetamide (-NHCOCH3). This step ensures selective reactivity of the methyl group.

Step 3: Oxidize the methyl group (-CH3) to a carboxylic acid (-COOH). This can be done using a strong oxidizing agent such as potassium permanganate (KMnO4) or chromic acid (H2CrO4). The methyl group is converted to a benzoic acid derivative.

Step 4: Remove the protecting group from the amino group (-NHCOCH3) to regenerate the free amino group (-NH2). This can be achieved by hydrolysis using either acidic or basic conditions, such as HCl or NaOH.

Step 5: Verify the structure of the final compound to ensure that the desired functional groups are correctly positioned and the transformations are complete. The final product should have a carboxylic acid (-COOH) and an amino group (-NH2) in the meta positions relative to each other on the benzene ring.

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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 are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. They can act as nucleophiles due to the lone pair of electrons on the nitrogen atom, making them reactive in various organic reactions, including alkylation and acylation. Understanding the reactivity of amines is crucial for predicting the products of reactions involving m-toluidine.

Electrophilic Aromatic Substitution (EAS)

Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the case of m-toluidine, the amino group (-NH2) is an activating group that directs electrophiles to the ortho and para positions of the aromatic ring. This concept is essential for understanding how to modify the aromatic structure of m-toluidine to form desired products.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule. In organic chemistry, this often refers to the conversion of functional groups, such as the reduction of nitro groups to amines or the reduction of carbonyls to alcohols. Knowing the types of reducing agents and their mechanisms is vital for transforming m-toluidine into other compounds, especially when considering the functional groups present in the target products.

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Related Practice

Textbook Question

Show how you would accomplish the following synthetic conversions.

(b) 1-bromo-2-phenylethane → 3-phenylpropan-1-amine

Textbook Question

Synthesize from benzene. (Hint: All of these require diazonium ions.)

(d) 4-methoxyaniline

Textbook Question

Synthesize from benzene. (Hint: All of these require diazonium ions.)

Textbook Question

Synthesize Novocaine from benzene and any other reagents of four carbons or fewer.

Textbook Question

Show how you would accomplish the following synthetic conversions.

(d) pentanoic acid → hexan-1-amine

Textbook Question

Show how you would accomplish the following synthetic conversions.

(e) (R)-2-bromobutane → (S)-butan-2-amine

Textbook Question

Show how you can synthesize the following tertiary amine three different ways, each using a different secondary amine and adding the final substituent by (b) acylation–reduction (3 ways).

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.

(a) benzoic acid → benzylamine

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

Key Concepts

Amines and Their Reactivity

Electrophilic Aromatic Substitution (EAS)

Reduction Reactions

Watch next

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

(b)