Textbook Question
Identify the functional groups in cocaine
Ch.16 Amines
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
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Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook
Chapter 16, Problem 36c
Give names or structures for the following ammonium salts. Indicate whether each is the ammonium salt of a primary, secondary, or tertiary amine.
c. N-Butyl-N-isopropylhexylammonium chloride
Verified step by step guidance1
Step 1: Understand the structure of the ammonium salt. The name 'N-Butyl-N-isopropylhexylammonium chloride' indicates that the compound is a quaternary ammonium salt, meaning the nitrogen atom is bonded to four alkyl groups and carries a positive charge, balanced by a chloride ion (Cl⁻).
Step 2: Break down the name into its components. 'N-Butyl' refers to a butyl group (C₄H₉) attached to the nitrogen atom. 'N-Isopropyl' refers to an isopropyl group (C₃H₇) attached to the nitrogen atom. 'Hexyl' refers to a hexyl group (C₆H₁₃) also attached to the nitrogen atom.
Step 3: Recognize the ammonium ion. Since the nitrogen atom is bonded to four alkyl groups (butyl, isopropyl, hexyl, and a fourth hydrogen atom), it forms a positively charged ammonium ion (R₄N⁺).
Step 4: Identify the counterion. The chloride ion (Cl⁻) is the counterion that balances the positive charge of the ammonium ion, forming the complete salt.
Step 5: Classify the amine type. Since the nitrogen atom is bonded to four groups (making it a quaternary ammonium ion), this is not a primary, secondary, or tertiary amine. Instead, it is a quaternary ammonium salt.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ammonium Salts
Ammonium salts are ionic compounds formed from the protonation of an amine, resulting in a positively charged ammonium ion (NH4+). They typically consist of an ammonium cation and a negatively charged anion, such as chloride. Understanding the structure of ammonium salts is crucial for identifying their properties and applications in various chemical contexts.
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Drawing Ammonium Salts Concept 2
Amines Classification
Amines are classified based on the number of carbon groups attached to the nitrogen atom. Primary amines have one carbon group, secondary amines have two, and tertiary amines have three. This classification affects the reactivity and properties of the amines, which is essential for determining the type of ammonium salt formed when they are protonated.
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Nomenclature of Organic Compounds
The nomenclature of organic compounds follows specific rules set by the International Union of Pure and Applied Chemistry (IUPAC). For ammonium salts, the name typically reflects the structure of the amine and the anion. Understanding these naming conventions is vital for accurately identifying and communicating the chemical nature of compounds like N-Butyl-N-isopropylhexylammonium chloride.
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Related Practice
Textbook Question
Draw the structures of the ammonium ions formed when the amines in Problem 16.30 are treated with acid.
a. N-Methylpentylamine
b. N-Ethylcyclobutylamine
c. p-Propylaniline
Textbook Question
Give names or structures for the following ammonium salts. Indicate whether each is the ammonium salt of a primary, secondary, or tertiary amine.
a.
Textbook Question
Complete the following equations (hint: remember that a nitrogen with three groups bound to it has a lone pair and one with four does not):
a.
Textbook Question
Give names or structures for the following ammonium salts. Indicate whether each is the ammonium salt of a primary, secondary, or tertiary amine.
a.
Textbook Question
Name the following amines, and identify them as primary, secondary, or tertiary:
b.