Textbook Question
Which of the following alcohols can undergo oxidation? Draw the line structure of the product expected for those that can. Assume an excess of oxidizing agent is present.
a.
b.
c.
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Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen
McMurry8th EditionFundamentals of GOBISBN: 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
Chapter 14, Problem 51
What is the structural relationship between a thiol and an alcohol?
Verified step by step guidance1
Understand the functional groups: An alcohol contains a hydroxyl group (-OH) attached to a carbon atom, while a thiol contains a sulfhydryl group (-SH) attached to a carbon atom.
Compare the elements involved: In an alcohol, the oxygen atom in the hydroxyl group is replaced by a sulfur atom in the sulfhydryl group of a thiol.
Recognize the structural similarity: Both alcohols and thiols have a single bond between the functional group and the carbon atom, making them structurally analogous.
Identify the key difference: The primary difference lies in the electronegativity and bonding properties of oxygen (in alcohols) versus sulfur (in thiols), which can affect their chemical behavior.
Conclude the relationship: Thiols and alcohols are functional group analogs, with sulfur in thiols replacing oxygen in alcohols, leading to similar but distinct chemical properties.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Thiol
A thiol is an organic compound that contains a sulfur atom bonded to a hydrogen atom (-SH group), making it a functional group similar to alcohols. Thiols are characterized by their strong odors and are often found in biological systems, where they play roles in enzyme function and protein structure.
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Reactions of Thiols Example 1
Alcohol
An alcohol is an organic compound that features one or more hydroxyl groups (-OH) attached to a carbon atom. Alcohols are widely used in various applications, including as solvents, fuels, and in the production of beverages. The presence of the hydroxyl group is key to their chemical properties and reactivity.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The structural relationship between thiols and alcohols lies in their functional groups; both contain a heteroatom (sulfur in thiols and oxygen in alcohols) bonded to hydrogen, influencing their reactivity and properties in organic chemistry.
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Related Practice
Textbook Question
The following alkenes can be prepared by dehydration of an appropriate alcohol. Show the structure of the alcohol in each case that would provide the alkene shown as the major product.
e. 1,4-Pentadiene
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Textbook Question
What alcohols would you oxidize to obtain the following carbonyl compounds?
a.
b.
c.
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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
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.
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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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