Domanda del libro di testo
Excess ammonia must be used when a primary amine is synthesized by reductive amination. What product will be obtained if the reaction is carried out with excess carbonyl compound?
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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 36
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 36Capitolo 16, Problema 36
Hydration of an aldehyde is also catalyzed by hydroxide ion. Propose a mechanism for the reaction.
Guida verificata passo dopo passo1
The first step in the mechanism is the nucleophilic attack of the hydroxide ion (OH⁻) on the carbonyl carbon of the aldehyde. This occurs because the carbonyl carbon is electrophilic due to the partial positive charge caused by the electronegativity difference between carbon and oxygen.
As the hydroxide ion attacks the carbonyl carbon, the π-electrons of the C=O bond are pushed onto the oxygen atom, creating a tetrahedral intermediate. This intermediate has a negatively charged oxygen atom (alkoxide ion).
In the next step, the negatively charged oxygen atom (alkoxide) abstracts a proton (H⁺) from water (H₂O), which acts as a proton donor. This step neutralizes the negative charge on the oxygen and forms a geminal diol (a compound with two hydroxyl groups attached to the same carbon).
The reaction is reversible, and the equilibrium between the aldehyde and the geminal diol is influenced by the stability of the aldehyde and the reaction conditions (e.g., pH, solvent).
The hydroxide ion acts as a catalyst in this reaction, as it is regenerated at the end of the mechanism. This means that the hydroxide ion facilitates the reaction without being consumed in the process.
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Aldehyde Structure and Reactivity
Aldehydes are organic compounds characterized by the presence of a carbonyl group (C=O) at the end of a carbon chain. This structure makes them highly reactive, particularly in nucleophilic addition reactions. Understanding the electrophilic nature of the carbonyl carbon is crucial, as it is susceptible to attack by nucleophiles, such as water in hydration reactions.
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01:34
Name the aldehyde
Nucleophilic Addition Mechanism
The nucleophilic addition mechanism involves the attack of a nucleophile on the electrophilic carbon of a carbonyl group. In the case of aldehydes, hydroxide ions (OH-) can act as nucleophiles, leading to the formation of a tetrahedral intermediate. This intermediate can then undergo protonation to yield the corresponding alcohol, illustrating the transformation of the aldehyde into a hydrated form.
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08:27Nucleophilic Addition
Role of Hydroxide Ion as a Catalyst
Hydroxide ions can catalyze the hydration of aldehydes by facilitating the nucleophilic attack on the carbonyl carbon. As a base, OH- can enhance the reactivity of water, allowing for a more efficient formation of the tetrahedral intermediate. This catalytic role is essential in organic reactions, as it lowers the activation energy and increases the reaction rate without being consumed in the process.
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Percorso guidato
3:39Metal Ion Catalysis Concept 1
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