Domanda del libro di testo
Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.
(c) octan-1-ol → decan-2-one
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Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- 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
Capitolo 21, Problema 39a
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
Guida verificata passo dopo passo1
Step 1: Convert hexan-1-ol to hexanenitrile. This can be achieved by first converting hexan-1-ol to hexyl bromide (or another alkyl halide) using PBr₃ or HBr. Then, perform a nucleophilic substitution reaction with NaCN or KCN to introduce the nitrile group, forming hexanenitrile.
Step 2: Extend the carbon chain of hexanenitrile by one carbon atom. This can be done using a Grignard reagent (e.g., CH₃MgBr) to react with the nitrile group, forming an imine intermediate.
Step 3: Hydrolyze the imine intermediate to form a ketone. This can be achieved by treating the imine with water under acidic conditions.
Step 4: Reduce the ketone to a primary amine. Use a reducing agent such as LiAlH₄ or catalytic hydrogenation (H₂/Pd) to convert the ketone to heptan-1-amine.
Step 5: Verify the structure of the final product, heptan-1-amine, ensuring that the carbon chain has been extended by one carbon and the functional group has been converted to an amine.
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Nitrile Chemistry
Nitriles are organic compounds containing a cyano group (-C≡N) and can serve as versatile intermediates in organic synthesis. They can be converted into various functional groups, including amines, through hydrolysis or reduction. Understanding the reactivity of nitriles is crucial for designing synthetic pathways, as they can facilitate the transformation of alcohols to amines.
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01:01
Nitrile Nomenclature
Reduction Reactions
Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule. In the context of nitriles, they can be reduced to primary amines using reagents such as lithium aluminum hydride (LiAlH4) or hydrogen gas in the presence of a catalyst. Recognizing the appropriate reducing agents is essential for successfully converting nitriles into amines.
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07:12Reductive Amination
Synthetic Pathways
Synthetic pathways are sequences of chemical reactions that transform reactants into desired products. In this case, the pathway from hexan-1-ol to heptan-1-amine involves the formation of a nitrile intermediate. Understanding how to construct these pathways, including the selection of reagents and reaction conditions, is vital for achieving the desired transformation efficiently.
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Percorso guidato
2:13Energy Production In Biochemical Pathways Concept 1
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