Textbook Question
Propose a mechanism to show the individual alkylations that form this quaternary ammonium salt.
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Ch. 19 - Amines
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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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 19, Problem 17
Give the products expected from the following reactions.
(a) acetyl chloride + ethylamine
(b) 
(c) 
Verified step by step guidance1
Step 1: Recognize that the reactions involve acyl chlorides reacting with amines. Acyl chlorides are highly reactive and undergo nucleophilic acyl substitution with amines to form amides.
Step 2: For reaction (i), acetyl chloride (CH3COCl) reacts with ethylamine (CH3NH2). The nucleophilic nitrogen in ethylamine attacks the carbonyl carbon of acetyl chloride, displacing the chloride ion (Cl⁻) and forming N-ethylacetamide.
Step 3: For reaction (ii), benzoyl chloride (C6H5COCl) reacts with piperidine (a cyclic secondary amine). The nitrogen in piperidine attacks the carbonyl carbon of benzoyl chloride, displacing the chloride ion and forming N-piperidinobenzamide.
Step 4: For reaction (iii), hexanoyl chloride (C6H13COCl) reacts with piperidine. The nitrogen in piperidine attacks the carbonyl carbon of hexanoyl chloride, displacing the chloride ion and forming N-piperidinohexanamide.
Step 5: In all cases, the byproduct of the reaction is hydrochloric acid (HCl), which forms due to the release of the chloride ion (Cl⁻) and protonation of the amine group.
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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 carbonyl carbon of an acyl compound, leading to the replacement of a leaving group (like a halide) with the nucleophile. This reaction is crucial for understanding how acyl chlorides react with amines, resulting in the formation of amides.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Acyl Chlorides
Acyl chlorides, also known as acid chlorides, are reactive compounds derived from carboxylic acids by replacing the hydroxyl group with a chlorine atom. Their high reactivity makes them important intermediates in organic synthesis, particularly in the formation of amides when reacted with amines, as seen in the provided reactions.
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01:57Recognizing acyl chlorides and anhydrides.
Amide Formation
Amide formation occurs when an amine reacts with an acyl chloride, resulting in the creation of an amide bond. This reaction typically involves the nucleophilic attack of the amine on the carbonyl carbon of the acyl chloride, followed by the elimination of hydrochloric acid. Understanding this process is essential for predicting the products of the reactions shown in the question.
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Related Practice
Textbook Question
Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.
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Textbook Question
(b) When 3-bromopyridine is used in this reaction, stronger reaction conditions are required and a mixture of 3-aminopyridine and 4-aminopyridine results. Propose a mechanism to explain this curious result.
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Textbook Question
Show how you would use direct alkylation to synthesize the following compounds.
(a) benzyltrimethylammonium iodide
(b) pentan-1-amine
(c) benzylamine
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Textbook Question
What would happen in the synthesis of sulfanilamide if the amino group were not protected as an amide in the chlorosulfonation step?
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