Textbook Question
What alcohols would you oxidize to obtain the following carbonyl compounds?
a.
b.
c.
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Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen
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 14, Problem 54
The boiling point of propanol is 97 °C ,much higher than that of either ethanethiol (37 °C) or chloroethane (13 °C) , even though all three compounds have similar MWs. Explain.
Verified step by step guidance1
Step 1: Identify the molecular structures of the three compounds: Propanol (C3H8O), Ethanethiol (C2H6S), and Chloroethane (C2H5Cl). Note that all three have similar molecular weights but differ in functional groups.
Step 2: Explain the concept of intermolecular forces. Intermolecular forces include hydrogen bonding, dipole-dipole interactions, and London dispersion forces. The strength of these forces determines the boiling point of a substance.
Step 3: Analyze the functional groups in each compound. Propanol contains an -OH group, which allows for hydrogen bonding. Ethanethiol contains an -SH group, which is less electronegative than oxygen and forms weaker hydrogen bonds. Chloroethane contains a -Cl group, which primarily exhibits dipole-dipole interactions and London dispersion forces.
Step 4: Discuss the impact of hydrogen bonding on boiling points. Hydrogen bonding is the strongest intermolecular force among the three compounds. Propanol's ability to form hydrogen bonds significantly increases its boiling point compared to ethanethiol and chloroethane.
Step 5: Conclude that the higher boiling point of propanol is due to the presence of strong hydrogen bonding from its -OH group, whereas ethanethiol and chloroethane lack this capability, resulting in lower boiling points despite similar molecular weights.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrogen Bonding
Hydrogen bonding is a strong type of dipole-dipole interaction that occurs when hydrogen is bonded to highly electronegative atoms like oxygen or nitrogen. In propanol, the presence of an -OH (hydroxyl) group allows for extensive hydrogen bonding between molecules, significantly raising its boiling point compared to ethanethiol and chloroethane, which lack such strong intermolecular forces.
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Molecular Weight vs. Boiling Point
While molecular weight can influence boiling points, it is not the sole determinant. Compounds with similar molecular weights can exhibit vastly different boiling points due to variations in intermolecular forces. In this case, propanol's higher boiling point is attributed to its ability to form hydrogen bonds, whereas ethanethiol and chloroethane rely on weaker van der Waals forces.
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Intermolecular Forces
Intermolecular forces are the forces of attraction or repulsion between molecules, which significantly affect physical properties like boiling points. Propanol's strong hydrogen bonds lead to higher boiling points, while ethanethiol and chloroethane, which primarily exhibit weaker London dispersion forces and dipole-dipole interactions, have lower boiling points despite similar molecular weights.
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Related Practice
Textbook Question
What is the structural relationship between a thiol and an alcohol?
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Textbook Question
Oxidation of a dithiol such as 2,5-hexanedithiol forms a six-membered ring containing a disulfide group as part of the ring. Draw the structure of this cyclic disulfide (Hint: Draw the starting compound in line structure format first).
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Textbook Question
Propanol is very soluble in water, but ethanethiol and chloroethane are only slightly soluble. Explain.
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Textbook Question
Define the following terms:
b. Achiral
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Textbook Question
Define the following terms:
c. Chiral carbon
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