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 18
What would happen in the synthesis of sulfanilamide if the amino group were not protected as an amide in the chlorosulfonation step?
Verified step by step guidance1
Understand the role of the amino group in the reaction: The amino group (-NH2) is highly nucleophilic, meaning it can readily react with electrophiles. In the chlorosulfonation step, the electrophilic reagent (e.g., chlorosulfonic acid, ClSO3H) would target nucleophilic sites in the molecule.
Recognize the purpose of protecting groups: Protecting the amino group as an amide (e.g., acetamide) reduces its nucleophilicity, preventing it from reacting with the chlorosulfonic acid. This ensures that the sulfonation occurs selectively at the desired position on the aromatic ring.
Predict the outcome without protection: If the amino group is not protected, it would likely react with the chlorosulfonic acid, forming undesired byproducts such as sulfonamides or other derivatives. This would interfere with the intended sulfonation of the aromatic ring.
Consider the impact on the synthesis: The formation of byproducts would reduce the yield of the desired sulfanilamide and complicate the purification process. Additionally, the reaction might not proceed efficiently due to competing side reactions.
Conclude the importance of protection: Protecting the amino group as an amide ensures the reaction proceeds with high selectivity and efficiency, leading to the successful synthesis of sulfanilamide. This highlights the critical role of protecting groups in multi-step organic syntheses.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Chlorosulfonation
Chlorosulfonation is a chemical reaction where a sulfonyl chloride group is introduced into an organic molecule using chlorosulfonic acid. This process is crucial in the synthesis of sulfanilamide, as it allows for the introduction of a sulfonamide functional group. If the amino group is not protected, it may react with the chlorosulfonic acid, leading to unwanted side reactions and potentially altering the desired product.
Protection of Functional Groups
In organic synthesis, protecting groups are used to temporarily mask reactive functional groups to prevent them from participating in unwanted reactions. In the case of sulfanilamide synthesis, protecting the amino group as an amide ensures that it remains unreactive during the chlorosulfonation step. This strategy is essential for maintaining the integrity of the desired product and achieving a successful synthesis.
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Protecting Groups
Sulfanilamide Structure and Function
Sulfanilamide is a sulfonamide antibiotic that contains an amino group and a sulfonamide group. The specific arrangement of these functional groups is critical for its biological activity. If the amino group is not protected during synthesis, it could lead to the formation of byproducts or alter the sulfanilamide structure, potentially affecting its efficacy as an antibiotic.
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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
Give the products expected from the following reactions.
(a) acetyl chloride + ethylamine
(b)
(c)
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Textbook Question
Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.
(a) hexan-2-amine
(b) 2-methylpiperidine
(c) N-ethylpiperidine
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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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