Textbook Question
Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize (i) benzyl acetate and (ii) N,N-diethylacetamide.
Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
Table of contents
- 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
Chapter 21, Problem 9c,d
Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(c) cyclohexanecarboxamide
(d) 
Verified step by step guidance1
Step 1: Understand the structure of the target amides. For cyclohexanecarboxamide (part c), the amide consists of a cyclohexane ring attached to a carboxamide group (-CONH2). For part d, analyze the provided structure in the image to identify the acyl chloride and amine components required.
Step 2: Identify the acyl chloride precursor. To synthesize cyclohexanecarboxamide, the acyl chloride precursor would be cyclohexanecarbonyl chloride (C6H11COCl). For part d, examine the structure in the image to determine the aromatic acyl chloride precursor.
Step 3: Identify the amine precursor. For cyclohexanecarboxamide, the amine precursor is ammonia (NH3), which reacts with the acyl chloride to form the amide. For part d, analyze the structure in the image to identify the specific amine required (e.g., a cyclic amine or aromatic amine).
Step 4: Write the reaction mechanism. The synthesis involves a nucleophilic acyl substitution reaction. The amine attacks the carbonyl carbon of the acyl chloride, leading to the formation of the amide and the release of HCl as a byproduct.
Step 5: Ensure proper reaction conditions. The reaction typically requires a base (e.g., pyridine) to neutralize the HCl byproduct and facilitate the formation of the amide. Confirm the reaction conditions for both parts c and d based on the structures provided.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
6mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acyl Chlorides
Acyl chlorides, also known as acid chlorides, are reactive derivatives of carboxylic acids where the hydroxyl group is replaced by a chlorine atom. They are highly reactive towards nucleophiles, making them useful in organic synthesis, particularly for forming amides. In the context of the question, acyl chlorides can be used to react with amines to produce the desired amides through nucleophilic acyl substitution.
Recommended video:
Guided course
01:57
Recognizing acyl chlorides and anhydrides.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of a leaving group. In the case of acyl chlorides, the leaving group is chloride, and the nucleophile can be an amine. This reaction is crucial for synthesizing amides, as it allows for the formation of a carbon-nitrogen bond while releasing HCl as a byproduct.
Recommended video:
Guided course
01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Amides
Amides are organic compounds characterized by the presence of a carbonyl group (C=O) directly attached to a nitrogen atom (N). They can be synthesized from carboxylic acids or their derivatives, such as acyl chlorides, by reacting with amines. Amides are important in both biological systems and synthetic chemistry, serving as building blocks for proteins and pharmaceuticals, and their formation is a key reaction in organic synthesis.
Recommended video:
Guided course
01:33Amide Nomenclature
Related Practice
Textbook Question
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(c) benzyl benzoate
(d) cyclopropyl cyclohexanecarboxylate
2
views
Textbook Question
Propose a mechanism for the reaction of benzyl acetate with methylamine. Label the attacking nucleophile and the leaving group, and draw the transition state in which the leaving group leaves.
1
views
Textbook Question
When ethyl 4-hydroxybutyrate is heated in the presence of a trace of a basic catalyst (sodium acetate), one of the products is a lactone. Propose a mechanism for formation of this lactone.
6
views
Textbook Question
Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.
(a) N,N-dimethylacetamide
(b) acetanilide (PhNHCOCH3)
1
views
Textbook Question
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(e) tert-butyl acetate
(f) diallyl succinate