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

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2:32 minutes

Problem 40a

Textbook Question

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

(a)

Verified step by step guidance

Step 1: Begin with m-toluidine (C6H4(CH3)(NH2)), which contains an amino group (-NH2) and a methyl group (-CH3) on the benzene ring in the meta position.

Step 2: Convert the amino group (-NH2) into a diazonium salt (-N2+). This is achieved by treating m-toluidine with sodium nitrite (NaNO2) and hydrochloric acid (HCl) at low temperatures (0–5°C). The reaction forms m-toluidine diazonium chloride.

Step 3: Replace the diazonium group (-N2+) with a cyano group (-CN) to form m-toluonitrile. This substitution is carried out using copper(I) cyanide (CuCN) in a Sandmeyer reaction. The diazonium salt reacts with CuCN to yield m-toluonitrile.

Step 4: Isolate and purify the m-toluonitrile product using standard organic chemistry techniques such as distillation or recrystallization.

Step 5: Verify the structure of m-toluonitrile using spectroscopic methods such as IR spectroscopy (to confirm the presence of the nitrile group, C≡N) and NMR spectroscopy (to confirm the positions of the substituents 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, such as m-toluidine, are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. They exhibit nucleophilic behavior due to the lone pair of electrons on the nitrogen atom, allowing them to 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 (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 is a strong activating group, directing incoming electrophiles to the ortho and para positions. This concept is essential for determining how m-toluidine can be modified to form various substituted aromatic compounds.

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, reduction, or substitution reactions to create desired products. Familiarity with common reagents and their effects on amines is vital for successfully planning the synthesis of the target compounds.

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Predict the product(s) of the reactions shown.

(b)

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The final step in the synthesis of diazoxide, a drug used to treat low blood pressure, is shown here. Suggest a mechanism for this step.

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The synthesis of ⍺-hydroxy acids can be done starting with amino acids. Suggest a mechanism of the two-step transformation shown. [The alcohol oxygen is the same in the reactant and product.

Textbook Question

Provide a mechanism for the protection of the amine as the benzylcarbamate shown in Figure 26.33(a). <IMAGE>

Textbook Question

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

(a) 3-ethylbenzoic acid

Textbook Question

Which would you expect to be a stronger nucleophile, ethyl amine or diethyl amine? Why?

Textbook Question

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

(b)

Textbook Question

Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.

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

Key Concepts

Amines and Their Reactivity

Electrophilic Aromatic Substitution (EAS)

Functional Group Transformations

Watch next

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

(a)