Domanda del libro di testo
Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.
3043
views
Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Non è quello che usi tu?Cambia libro di testoScegli un libro di testo diverso
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 6a
Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.
Guida verificata passo dopo passo1
Step 1: Identify the reactants and the product. Benzyl alcohol (C6H5CH2OH) reacts with acetyl chloride (CH3COCl) to form benzyl acetate (C6H5CH2OCOCH3). This is an esterification reaction where the hydroxyl group (-OH) of benzyl alcohol is replaced by an acetyl group (-COCH3).
Step 2: Recognize the role of acetyl chloride as an acylating agent. Acetyl chloride is highly reactive due to the presence of the carbonyl group (C=O) and the chlorine atom, which makes the carbonyl carbon electrophilic and susceptible to nucleophilic attack.
Step 3: Mechanism initiation: The lone pair of electrons on the oxygen atom of benzyl alcohol attacks the electrophilic carbonyl carbon of acetyl chloride. This forms a tetrahedral intermediate, and the chlorine atom is still attached to the carbonyl carbon.
Step 4: Collapse of the tetrahedral intermediate: The intermediate collapses, expelling the chloride ion (Cl⁻) as a leaving group. This results in the formation of the ester bond between the benzyl alcohol and the acetyl group.
Step 5: Final step: The chloride ion (Cl⁻) may react with a proton (H⁺) from the reaction medium to form HCl as a byproduct. The final product is benzyl acetate (C6H5CH2OCOCH3), an ester.
Risposta video verificata per un problema simile:
Questa soluzione video è stata consigliata dai nostri tutor come utile per risolvere questo problema.
Durata del video:
3mConcetti chiave
Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbonyl carbon, leading to the substitution of a leaving group. In this case, benzyl alcohol acts as the nucleophile, attacking the carbonyl carbon of acetyl chloride, which is a reactive acyl chloride. This mechanism is crucial for understanding how esters, like benzyl acetate, are formed from alcohols and acyl chlorides.
Video consigliato:
01:47
Nucleophiles and Electrophiles can react in Substitution Reactions.
Role of Leaving Groups
In organic reactions, leaving groups are atoms or groups that can depart with a pair of electrons, facilitating the formation of new bonds. In the reaction between benzyl alcohol and acetyl chloride, the chloride ion (Cl-) is the leaving group. A good leaving group is essential for the reaction to proceed efficiently, as it stabilizes the transition state and allows the nucleophile to bond with the electrophile.
Video consigliato:
07:22The 3 important leaving groups to know.
Formation of Esters
The formation of esters is a key reaction in organic chemistry, typically involving the reaction of an alcohol with a carboxylic acid or an acyl chloride. In this case, benzyl alcohol reacts with acetyl chloride to produce benzyl acetate. This reaction is significant in both synthetic organic chemistry and industrial applications, as esters are widely used in fragrances, flavorings, and as solvents.
Video consigliato:
02:39Ester Nomenclature
Pratica correlata
Domanda del libro di testo
Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.
(o)
(p)
536
views
Domanda del libro di testo
Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.
(q)
(r)
531
views
Domanda del libro di testo
Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.
2149
views
Domanda del libro di testo
Propose a second mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the other oxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.
713
views
Domanda del libro di testo
Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.
(m)
(n)
650
views