Textbook Question
Propose a mechanism for the synthesis of methyl orange.
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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 25a,b,c
Give the expected products of lithium aluminum hydride reduction of the following compounds (followed by hydrolysis).
(a) butyronitrile
(b) N-cyclohexylacetamide
(c) ε-caprolactam
Verified step by step guidance1
Identify the functional group in each compound and understand how lithium aluminum hydride (LiAlH₄) reduces it. LiAlH₄ is a strong reducing agent that reduces nitriles, amides, and lactams to their corresponding amines.
For (a) butyronitrile: Recognize that the nitrile group (-C≡N) will be reduced by LiAlH₄ to a primary amine (-CH₂NH₂). Write the reaction: CH₃CH₂CH₂C≡N → CH₃CH₂CH₂CH₂NH₂ after reduction and hydrolysis.
For (b) N-cyclohexylacetamide: Recognize that the amide group (-CONH-) will be reduced by LiAlH₄ to an amine. The carbonyl group (C=O) is removed, and the product will be N-cyclohexylethylamine. Write the reaction: C₆H₁₁NHCOCH₃ → C₆H₁₁NHCH₂CH₃ after reduction and hydrolysis.
For (c) ε-caprolactam: Recognize that the lactam (a cyclic amide) will be reduced by LiAlH₄ to a cyclic amine. The carbonyl group (C=O) in the lactam ring is removed, resulting in hexamethyleneimine. Write the reaction: (CH₂)₅C(O)NH → (CH₂)₅NH after reduction and hydrolysis.
Summarize the products: (a) butylamine (CH₃CH₂CH₂CH₂NH₂), (b) N-cyclohexylethylamine (C₆H₁₁NHCH₂CH₃), and (c) hexamethyleneimine ((CH₂)₅NH). Ensure to understand the role of hydrolysis in completing the reduction process.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Lithium Aluminum Hydride (LiAlH4) Reduction
Lithium aluminum hydride is a powerful reducing agent commonly used in organic chemistry to reduce various functional groups. It can convert nitriles, amides, and lactams into their corresponding amines by adding hydrogen across the multiple bonds. The reaction typically involves the nucleophilic attack of the hydride ion on the electrophilic carbon of the functional group, followed by hydrolysis to yield the final amine product.
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The Primary Amines Flowchart
Hydrolysis
Hydrolysis is a chemical reaction involving the breakdown of a compound due to reaction with water. In the context of LiAlH4 reductions, hydrolysis is crucial as it helps to convert the alkoxide intermediates formed during the reduction into stable alcohols or amines. This step is essential for isolating the final products after the reduction process.
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Functional Group Transformation
Functional group transformation refers to the process of converting one functional group into another through chemical reactions. In the case of the compounds mentioned, butyronitrile, N-cyclohexylacetamide, and e-caprolactam, the transformations involve the reduction of nitriles and amides to amines. Understanding the reactivity of these functional groups is key to predicting the products of the reduction reactions.
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Related Practice
Textbook Question
Show how you would convert aniline to the following compounds.
(a) fluorobenzene
(b) chlorobenzene
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Textbook Question
Show how you would convert aniline to the following compounds.
(f) benzonitrile
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Textbook Question
Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.
(d) aniline
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Textbook Question
Show how you would convert aniline to the following compounds.
(d) bromobenzene
(e) iodobenzene
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Textbook Question
Show how you would convert aniline to the following compounds.
(c) 1,3,5-trimethylbenzene
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