Textbook Question
Write the mechanism for each of the following reactions:
b. the reaction of benzoyl chloride with excess methylamine to form N-methylbenzamide
1578
views
Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- 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
All textbooks
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 12f
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 12fChapter 16, Problem 12f
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
f. 
Verified step by step guidance1
Step 1: Analyze the target compound. The structure shows an ester functional group, specifically an ethyl ester, attached to a benzene ring substituted with two nitro groups and a methyl group.
Step 2: Identify the starting material, acetyl chloride (CH3COCl). Acetyl chloride is an acyl chloride, which is reactive and can undergo nucleophilic acyl substitution reactions to form esters.
Step 3: Determine the neutral nucleophile required to form the ester. To synthesize the target compound, the nucleophile must be a phenol derivative with the same substitution pattern as the benzene ring in the target compound: a methyl group and two nitro groups.
Step 4: Select the appropriate phenol derivative. The nucleophile should be 2-methyl-4,6-dinitrophenol, as it matches the substitution pattern of the benzene ring in the target compound.
Step 5: Outline the reaction mechanism. Acetyl chloride reacts with 2-methyl-4,6-dinitrophenol in the presence of a base (such as pyridine) to neutralize the HCl byproduct. This results in the formation of the ester bond, yielding the target compound.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the context of acetyl chloride, the nucleophile must be neutral and capable of attacking the carbonyl carbon, leading to the formation of a new bond. Understanding this mechanism is crucial for predicting the products of reactions involving acetyl chloride.
Recommended video:
Guided course
01:47
Nucleophiles and Electrophiles can react in Substitution Reactions.
Acetyl Chloride Reactivity
Acetyl chloride is a reactive acyl chloride that can undergo nucleophilic acyl substitution due to the presence of the electron-withdrawing chlorine atom. This reactivity allows it to react with various nucleophiles, including alcohols and amines, to form esters and amides, respectively. Recognizing the reactivity of acetyl chloride helps in selecting appropriate nucleophiles for synthesizing desired compounds.
Recommended video:
Guided course
01:36Synthesis of Acid Chlorides
Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. In the compound shown, the presence of nitro groups indicates that the aromatic ring is activated for further substitution. Understanding EAS is essential for predicting how the aromatic system will react with nucleophiles, especially when considering the influence of substituents on the ring's reactivity.
Recommended video:
Guided course
03:07EAS Review
Related Practice
Textbook Question
Starting with methyl acetate, what neutral nucleophile would you use to synthesize each of the following compounds? a. ethyl acetate
1212
views
Textbook Question
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
e.
1147
views
Textbook Question
Write the mechanism for each of the following reactions:
a. the reaction of acetyl chloride with water to form acetic acid
713
views
Textbook Question
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
c.
1037
views
Textbook Question
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
d.
1050
views