Textbook Question
Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an SN2 reaction?
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 7
Which of the following proposed reactions would take place quickly under mild conditions?
(a) 
(b) 
(c) 
(d) 
(e) 
Verified step by step guidance1
Step 1: Analyze the reactivity of the functional groups in each reaction. Mild conditions typically favor reactions with highly reactive functional groups, such as acyl chlorides, which readily undergo nucleophilic substitution.
Step 2: Evaluate reaction (i). The reaction involves an amide and NaCl. Amides are relatively stable and do not react easily under mild conditions with NaCl, as this would require harsh conditions to break the C-N bond.
Step 3: Evaluate reaction (ii). The reaction involves an acyl chloride and methylamine (CH3NH2). Acyl chlorides are highly reactive and readily undergo nucleophilic substitution with amines under mild conditions, forming an amide and releasing HCl.
Step 4: Evaluate reaction (iii). The reaction involves an amide and ethanol (CH3CH2OH). Amides are stable and do not react easily with alcohols under mild conditions, as this would require strong acid or base catalysis.
Step 5: Evaluate reaction (iv) and (v). Reaction (iv) involves an acyl chloride and a carboxylic acid, which can react under mild conditions to form an anhydride. Reaction (v) involves an ester and ethylamine, which can react under mild conditions to form an amide and acetic acid. Both reactions are feasible under mild conditions.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
3mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the electrophilic carbon of a carbonyl group, leading to the replacement of a leaving group. This reaction is characteristic of carboxylic acid derivatives, such as esters, amides, and acyl chlorides. The rate of this reaction can be influenced by the nature of the nucleophile and the leaving group, as well as the reaction conditions.
Recommended video:
Guided course
01:47
Nucleophiles and Electrophiles can react in Substitution Reactions.
Leaving Groups
In nucleophilic acyl substitution reactions, the leaving group is the atom or group that departs with a pair of electrons, allowing the nucleophile to bond to the carbonyl carbon. Good leaving groups, such as halides (e.g., Cl, Br) or sulfonate esters, stabilize the transition state and facilitate the reaction. The ability of a leaving group to depart is crucial for determining the reaction's speed and feasibility under mild conditions.
Recommended video:
Guided course
07:22The 3 important leaving groups to know.
Reaction Conditions
Mild reaction conditions refer to the use of low temperatures, neutral pH, and non-aggressive solvents that do not promote side reactions or decomposition of reactants. These conditions are often preferred in organic synthesis to ensure selectivity and yield. Understanding how different conditions affect the reactivity of nucleophiles and electrophiles is essential for predicting which reactions will proceed quickly and efficiently.
Recommended video:
1:18EAS Reactions of Pyridine Example 1
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 aniline with acetic anhydride to give acetanilide.
1
views
Textbook Question
Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(a) ethyl propionate
(b) phenyl 3-methylhexanoate
1
views
Textbook Question
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.
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