Textbook Question
If a quaternary ammonium ion can undergo an elimination reaction with a strong base, why can’t a protonated tertiary amine undergo the same reaction?
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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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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
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Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 42
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 42Chapter 11, Problem 42
Explain why the half-life (the time it takes for one-half of the compound to be metabolized) of Xylocaine is longer than that of Novocaine.
Verified step by step guidance1
Identify the structural differences between Xylocaine (Lidocaine) and Novocaine (Procaine). Xylocaine contains an amide functional group, while Novocaine contains an ester functional group.
Understand the chemical stability of amides versus esters. Amides are more resistant to hydrolysis due to the partial double bond character of the C-N bond, which makes them less reactive to enzymatic breakdown.
Recognize the role of esterases in the body. Esterases are enzymes that rapidly hydrolyze ester bonds, leading to faster metabolism of compounds like Novocaine.
Consider the metabolic pathways. Xylocaine, with its amide bond, is metabolized primarily in the liver by cytochrome P450 enzymes, which is a slower process compared to the rapid hydrolysis of Novocaine by esterases in the plasma.
Conclude that the longer half-life of Xylocaine is due to its amide bond, which is more chemically stable and metabolized more slowly than the ester bond in Novocaine.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Half-Life
Half-life is the time required for the concentration of a substance to reduce to half its initial value. In pharmacology, it is crucial for understanding how long a drug remains active in the body. The half-life can be influenced by factors such as metabolism, elimination pathways, and the drug's chemical structure.
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Organic molecules in your everyday life.
Metabolism of Drugs
Drug metabolism refers to the biochemical modification of pharmaceutical substances by living organisms, primarily through enzymatic activity. The rate of metabolism can vary significantly between different drugs due to their chemical properties and the pathways they undergo, affecting their half-lives. Understanding the metabolic pathways of Xylocaine and Novocaine is essential to explain their differing half-lives.
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Chemical Structure and Properties
The chemical structure of a drug influences its solubility, stability, and interaction with metabolic enzymes. Xylocaine (lidocaine) and Novocaine (procaine) have different molecular structures, which can lead to variations in their absorption, distribution, and elimination. These structural differences are key to understanding why Xylocaine has a longer half-life compared to Novocaine.
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Related Practice
Textbook Question
Three arene oxides can be obtained from phenanthrene.
a. Draw the structures of the three phenanthrene oxides.
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Textbook Question
What are the major products of the following reaction?
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Textbook Question
Three arene oxides can be obtained from phenanthrene.
d. Which of the three phenanthrene oxides is most likely to be carcinogenic?
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Textbook Question
What are the minor products of the preceding Hofmann elimination reaction?
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Textbook Question
Three arene oxides can be obtained from phenanthrene.
c. If a phenanthrene oxide can lead to the formation of more than one phenol, which phenol will be obtained in greater yield?
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