Textbook Question
Explain what bonds must be made or broken and where the electrons go when the hydrogen-bonded water between the two amines shown on page 507 reacts to form an amine, ammonium ion, and OH⁻.
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 24b
The structure of the amino acid lysine (in its uncharged form) is shown below.
b. Is lysine likely to be water-soluble? Explain.
Verified step by step guidance1
Step 1: Understand the structure of lysine. Lysine is an amino acid with a side chain containing an amino group (-NH2) attached to a long hydrocarbon chain. It also has the general structure of amino acids, which includes an amino group (-NH2), a carboxyl group (-COOH), and a central carbon atom bonded to a hydrogen atom and the side chain.
Step 2: Recall the concept of solubility. A molecule's solubility in water depends on its ability to form hydrogen bonds with water molecules. Polar or charged groups in a molecule increase its water solubility because they can interact with water's polar nature.
Step 3: Analyze the functional groups in lysine. Lysine contains polar functional groups, such as the amino group (-NH2) and the carboxyl group (-COOH), which can form hydrogen bonds with water. Additionally, the side chain of lysine has another amino group (-NH2), which is also polar and capable of hydrogen bonding.
Step 4: Consider the overall polarity of lysine. Despite the presence of a hydrocarbon chain in the side chain, the multiple polar groups dominate, making lysine a polar molecule overall. This polarity enhances its interaction with water.
Step 5: Conclude based on the analysis. Since lysine has several polar groups capable of forming hydrogen bonds with water, it is likely to be water-soluble. The presence of these groups outweighs the nonpolar hydrocarbon chain in the side chain.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Amino Acid Structure
Amino acids are organic compounds composed of an amino group, a carboxyl group, and a unique side chain (R group). The structure of lysine includes a positively charged amino group in its side chain, which influences its interactions with water and other molecules. Understanding the basic structure of amino acids is essential for predicting their solubility and behavior in biological systems.
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Polarity and Solubility
Polarity refers to the distribution of electrical charge around atoms, molecules, or chemical groups. Water is a polar solvent, meaning it dissolves other polar substances well. Lysine, with its polar amino and carboxyl groups, is likely to interact favorably with water, making it water-soluble. This concept is crucial for understanding how amino acids behave in aqueous environments.
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Hydrophilic vs. Hydrophobic
Hydrophilic molecules are attracted to water and tend to dissolve in it, while hydrophobic molecules repel water and do not dissolve easily. Lysine, due to its polar side chain and functional groups, is classified as hydrophilic. This classification helps explain why lysine is likely to be water-soluble, as hydrophilic substances readily interact with the polar nature of water.
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Related Practice
Textbook Question
Complete the following equations:
b.
Textbook Question
Write the structure of benzylamine hydrochloride in two different ways, and name the hydrochloride as an ammonium salt.
Textbook Question
The structure of the amino acid lysine (in its uncharged form) is shown below.
a. Which amine groups would be able to participate in hydrogen bonding?
Textbook Question
Draw the structures corresponding to the following names:
a. N-Methylpentylamine
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Textbook Question
a. For the compound above, identify each nitrogen as either a primary, secondary, tertiary, quaternary, or aromatic amine.