Textbook Question
Show how m-toluidine can be converted to the following compounds, using any necessary reagents.
(e)
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Ch. 19 - Amines
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 19, Problem 42a
Using any necessary reagents, show how you would accomplish the following syntheses.
(a) 
Verified step by step guidance1
Step 1: Begin with benzene as the starting material. Perform a Friedel-Crafts acylation reaction using an acyl chloride (e.g., cyclohexanecarbonyl chloride) and a Lewis acid catalyst such as AlCl₃. This will introduce the cyclohexanecarbonyl group onto the benzene ring, forming phenyl cyclohexyl ketone.
Step 2: Reduce the ketone group to a methylene group using a reducing agent such as Clemmensen reduction (Zn/HCl) or Wolff-Kishner reduction (hydrazine and KOH). This step is optional if the ketone group is already desired.
Step 3: Introduce an amine group onto the benzene ring. This can be achieved by nitration of benzene (using HNO₃ and H₂SO₄) to form nitrobenzene, followed by reduction of the nitro group to an amine group using a reducing agent like Sn/HCl or catalytic hydrogenation.
Step 4: Perform an acylation reaction on the amine group using cyclohexanecarbonyl chloride. This will form the desired amide bond between the amine group and the cyclohexanecarbonyl group.
Step 5: Verify the structure of the final product, N-cyclohexylbenzamide, ensuring that the amide bond is correctly formed and the cyclohexyl group is attached to the carbonyl carbon.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acylation
Acylation is a chemical reaction that introduces an acyl group (RCO-) into a molecule. In organic synthesis, this process often involves the reaction of an amine, such as aniline, with an acyl chloride or an acid anhydride. The result is the formation of an amide, which is characterized by the presence of a carbonyl group adjacent to a nitrogen atom. This reaction is crucial for modifying the properties of organic compounds.
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05:20
Friedel-Crafts Acylation
Reagents in Organic Synthesis
Reagents are substances used to cause a chemical reaction or to test for the presence of another substance. In the context of acylation, common reagents include acyl chlorides (like acetyl chloride) and acid anhydrides. The choice of reagent can influence the reaction's efficiency, selectivity, and the nature of the final product. Understanding the role of these reagents is essential for successful organic synthesis.
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Mechanism of Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental mechanism in organic chemistry where a nucleophile attacks an electrophilic carbonyl carbon, leading to the substitution of a leaving group. In the case of acylation of aniline, the nitrogen atom of the amine acts as the nucleophile, attacking the carbonyl carbon of the acyl chloride. This mechanism is vital for understanding how acylation reactions proceed and the formation of amides from amines.
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Related Practice
Textbook Question
Using any necessary reagents, show how you would accomplish the following syntheses.
(b)
949
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Textbook Question
Show how m-toluidine can be converted to the following compounds, using any necessary reagents.
(f)
722
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Textbook Question
The mass spectrum of tert-butylamine follows shows an intense base peak at m/z 58, and very little else. Use a diagram to show the cleavage that accounts for the base peak. Suggest why no molecular ion is visible in this spectrum.
2045
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Textbook Question
Using any necessary reagents, show how you would accomplish the following syntheses.
(c)
1232
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Textbook Question
Using any necessary reagents, show how you would accomplish the following syntheses.
(d)
620
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