Domanda del libro di testo
Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.
(a) propiophenone from propionic acid (using Friedel–Crafts acylation)
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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 20b
Propose a mechanism for the hydrolysis of N,N-dimethylacetamide
(b) under acidic conditions.
Guida verificata passo dopo passo1
Step 1: Protonation of the carbonyl oxygen - Under acidic conditions, the lone pair of electrons on the oxygen atom of the carbonyl group in N,N-dimethylacetamide will interact with a proton (H⁺) from the acid, leading to the formation of a protonated carbonyl group. This increases the electrophilicity of the carbonyl carbon.
Step 2: Nucleophilic attack by water - The water molecule acts as a nucleophile and attacks the electrophilic carbonyl carbon, forming a tetrahedral intermediate. This step involves the addition of water to the carbonyl group.
Step 3: Proton transfer - A proton transfer occurs within the tetrahedral intermediate to stabilize the structure. This step involves the movement of a proton from the water molecule to the nitrogen atom, making the leaving group more favorable.
Step 4: Cleavage of the C-N bond - The nitrogen atom, now protonated, becomes a good leaving group. The C-N bond breaks, leading to the formation of acetic acid and a protonated amine (N,N-dimethylamine).
Step 5: Deprotonation - The protonated amine loses a proton to regenerate the neutral amine (N,N-dimethylamine), and the acetic acid remains as the final product of the hydrolysis reaction.
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Hydrolysis Mechanism
Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the case of N,N-dimethylacetamide, the mechanism typically involves the nucleophilic attack of water on the carbonyl carbon, leading to the formation of a tetrahedral intermediate. This intermediate can then collapse, resulting in the formation of acetic acid and dimethylamine.
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Percorso guidato
0:55
Hydrolysis of Nucleosides Concept 1
Acidic Conditions
Acidic conditions refer to an environment where the pH is less than 7, often achieved by adding a strong acid like HCl. In hydrolysis reactions, acids can protonate the carbonyl oxygen, increasing the electrophilicity of the carbonyl carbon. This makes it more susceptible to nucleophilic attack by water, facilitating the hydrolysis process.
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02:23Using factors affecting acidity to rank acids
Nucleophilicity
Nucleophilicity is a measure of how readily a nucleophile donates an electron pair to form a chemical bond. In the hydrolysis of N,N-dimethylacetamide, water acts as a nucleophile. The presence of acidic conditions enhances the nucleophilicity of water by stabilizing the transition state, thus promoting the reaction with the electrophilic carbonyl carbon.
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08:27Nucleophilic Addition
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