Domanda del libro di testo
What are the products of the following reactions?
a.
b.
c.
d.
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 27
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 27Capitolo 16, Problema 27
A ketone can be prepared from the reaction of a nitrile with a Grignard reagent. Describe the intermediate formed in this reaction, and show how it can be converted to a ketone.
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The reaction begins with the nucleophilic attack of the Grignard reagent (R-MgX) on the carbon atom of the nitrile group (R'-C≡N). This carbon is electrophilic due to the polarization of the triple bond between carbon and nitrogen.
The nucleophilic attack results in the formation of an intermediate imine salt. The structure of this intermediate can be represented as R'-C=N⁻-MgX, where the nitrogen atom carries a negative charge and is bonded to the magnesium ion.
The imine salt intermediate is then hydrolyzed in the presence of water or an acidic workup. During hydrolysis, the imine group (C=N⁻) is converted into a carbonyl group (C=O).
The hydrolysis step involves protonation of the nitrogen atom, followed by the cleavage of the C=N bond and the addition of water to form a ketone (R'-C=O-R).
The final product of the reaction is a ketone, where the alkyl group from the Grignard reagent (R) is attached to the carbonyl carbon of the original nitrile (R'-C≡N).
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Grignard Reagents
Grignard reagents are organomagnesium compounds that act as nucleophiles in organic reactions. They are formed by the reaction of an alkyl or aryl halide with magnesium metal in anhydrous ether. In the context of the reaction with nitriles, Grignard reagents attack the electrophilic carbon of the nitrile, leading to the formation of a new carbon-carbon bond.
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02:12
Carbonation of Grignard Reagents
Nitrile Intermediate
When a Grignard reagent reacts with a nitrile, it forms an intermediate known as an imine or a ketimine, depending on the structure of the nitrile. This intermediate contains a carbon-nitrogen double bond and is crucial for the subsequent transformation into a ketone. The imine can be hydrolyzed to yield the corresponding ketone upon treatment with water or an acid.
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01:01Nitrile Nomenclature
Hydrolysis of Imines
Hydrolysis of imines involves the addition of water to the imine intermediate, leading to the cleavage of the carbon-nitrogen double bond. This reaction typically requires an acid catalyst to facilitate the process. The result is the formation of a ketone and the release of ammonia, completing the conversion from the nitrile to the ketone through the imine intermediate.
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06:23Imine Mechanism
Pratica correlata
Domanda del libro di testo
Imines can exist as stereoisomers. The isomers are named using the E,Z system of nomenclature (Section 4.2 ). The lone pair has the lowest priority.
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Draw the structure of each of the following compounds:
a. the (E)-hydrazone of benzaldehyde
b. the (Z)-oxime of propiophenone
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Domanda del libro di testo
Why is the pKa value of protonated hydroxylamine (6.0) so much lower than the value of a protonated primary amine such as protonated methylamine (10.7)?
1039
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Domanda del libro di testo
How would you make the following compounds from N-benzylbenzamide?
c. benzyl alcohol
1097
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Domanda del libro di testo
The pKa of protonated acetone is about –7.5 and the pKa of protonated hydroxylamine is 6.0.
a. In a reaction with hydroxylamine at pH 4.5 (Figure 16.2), what fraction of acetone is present in its acidic, protonated form?
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Domanda del libro di testo
How would you make the following compounds from N-benzylbenzamide?
b. benzoic acid
1077
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