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Predict the products of the following reactions.
(k)
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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 50j
Predict the products of the following reactions.
(j) 
Guida verificata passo dopo passo1
Step 1: Analyze the first reaction. The starting compound is a nitrile (cyclopentyl nitrile), and the reagents are CH3MgI (a Grignard reagent) followed by H3O+ (acidic hydrolysis). Grignard reagents react with nitriles to form imines, which are then hydrolyzed under acidic conditions to yield ketones.
Step 2: In the first reaction, the CH3MgI adds to the carbon of the nitrile group (C≡N), breaking the triple bond and forming an intermediate imine. The imine is then hydrolyzed by H3O+ to produce a ketone. The final product will be cyclopentyl methyl ketone.
Step 3: Analyze the second reaction. The starting compound is a lactam (cyclic amide), and the reagents are NaOH and H2O. Under basic conditions, lactams undergo hydrolysis to yield the corresponding amino acid.
Step 4: In the second reaction, NaOH breaks the amide bond in the lactam, resulting in the formation of a carboxylate group and an amine group. The product will be 6-aminocaproic acid (the open-chain form of the lactam).
Step 5: Summarize the transformations: (i) Cyclopentyl nitrile reacts with CH3MgI and H3O+ to form cyclopentyl methyl ketone. (ii) The lactam reacts with NaOH and H2O to yield 6-aminocaproic acid.
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Nitrile Reactivity
Nitriles are organic compounds containing a cyano group (-C≡N). They can undergo nucleophilic addition reactions, where a nucleophile attacks the carbon atom of the cyano group. In this case, CH3MgI (a Grignard reagent) acts as a strong nucleophile, adding a methyl group to the nitrile, ultimately leading to the formation of an intermediate that can be hydrolyzed to yield an amine.
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01:01
Nitrile Nomenclature
Grignard Reagents
Grignard reagents, such as CH3MgI, are organomagnesium compounds that are highly reactive and serve as nucleophiles in organic synthesis. They can react with electrophiles, such as carbonyls and nitriles, to form new carbon-carbon bonds. The reaction with a nitrile results in the formation of an imine intermediate, which can be further hydrolyzed to produce a primary amine after treatment with water or acid.
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02:12Carbonation of Grignard Reagents
Hydrolysis of Nitriles
Hydrolysis is the chemical process in which a compound reacts with water, leading to the breakdown of that compound. In the context of nitriles, after the addition of a Grignard reagent, the subsequent treatment with H3O+ (acidic water) facilitates the conversion of the intermediate into a carboxylic acid and an amine. This step is crucial for completing the transformation of the nitrile into a more functionalized product.
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Percorso guidato
1:09Review of Nitriles Concept 6
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