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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4:56 minutes

Problem 50g

Textbook Question

Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.
(g) 4-isobutylaniline

Verified step by step guidance

Step 1: Start with toluene as the base compound. Perform a Friedel-Crafts alkylation using isobutyl chloride (CH3CH(CH3)CH2Cl) and AlCl3 as the catalyst to introduce the isobutyl group at the para position relative to the methyl group. This step gives para-isobutyltoluene as the major product.

Step 2: Oxidize the methyl group on the benzene ring of para-isobutyltoluene to a carboxylic acid group. This can be achieved using a strong oxidizing agent such as potassium permanganate (KMnO4) under acidic or basic conditions. The product is para-isobutylbenzoic acid.

Step 3: Convert the carboxylic acid group to an amine group (-NH2) through a two-step process. First, reduce the carboxylic acid to a primary amide (-CONH2) using reagents like SOCl2 followed by NH3. Then, reduce the amide to an amine using a reducing agent such as lithium aluminum hydride (LiAlH4). This step yields 4-isobutylaniline.

Step 4: Purify the product to isolate 4-isobutylaniline. Since para is the major product, it can be separated from any minor ortho product using techniques like recrystallization or column chromatography.

Step 5: Verify the structure of the synthesized compound using spectroscopic techniques such as NMR (nuclear magnetic resonance) and IR (infrared spectroscopy) to confirm the presence of the isobutyl group and the amine group at the para position.

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Key Concepts

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

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. This reaction is crucial for synthesizing substituted aromatic compounds, such as 4-isobutylaniline, from benzene or toluene. Understanding the mechanism of EAS, including the role of activating and deactivating groups, is essential for predicting the outcome of the synthesis.

Nucleophilic Aromatic Substitution (NAS)

Nucleophilic Aromatic Substitution is a reaction where a nucleophile replaces a leaving group on an aromatic compound. This concept is particularly relevant when synthesizing compounds like 4-isobutylaniline, as it may involve the introduction of an amine group onto a substituted aromatic ring. Recognizing the conditions under which NAS occurs, such as the presence of electron-withdrawing groups, is vital for successful synthesis.

Functional Group Interconversion

Functional Group Interconversion refers to the transformation of one functional group into another, which is often necessary in organic synthesis. In the context of synthesizing 4-isobutylaniline, converting alcohols or alkyl groups into amines or other functional groups is essential. Mastery of various reactions, such as reduction or substitution, allows chemists to manipulate starting materials effectively to achieve desired products.

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Related Practice

Textbook Question

Give the expected products of lithium aluminum hydride reduction of the following compounds (followed by hydrolysis).

(a) butyronitrile

(b) N-cyclohexylacetamide

Textbook Question

Predict the products of the following reactions.

(e)

(f)

Textbook Question

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.

(a) hexan-1-ol → heptan-1-amine

Textbook Question

Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene and toluene as your aromatic starting materials.

(d) m-aminobenzoic acid

Textbook Question

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

(b)

Textbook Question

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide → benzylamine

Textbook Question

Several additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitro compounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds one carbon atom. Show how these amine syntheses can be used for the following conversions.

Textbook Question

Starting with cyclohexene, how can the following compounds be prepared?

b. cyclohexylmethylamine

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