Textbook Question
Draw structures for the following:
a. 2,4-Dinitrophenol
b. m-Ethylphenol
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 11
What products would you expect from oxidation of the following alcohols?
a. CH3CH2CH2OH
b. 
c. 
Verified step by step guidance1
Step 1: Understand the concept of alcohol oxidation. Oxidation of alcohols involves the loss of hydrogen atoms or the gain of oxygen atoms. The product depends on the type of alcohol: primary, secondary, or tertiary.
Step 2: Analyze the structure of the first alcohol (CH3CH2CH2OH). This is a primary alcohol because the hydroxyl group (-OH) is attached to a carbon atom that is bonded to only one other carbon atom.
Step 3: Recall the oxidation pathway for primary alcohols. Primary alcohols are oxidized to aldehydes (R-CHO) first, and with further oxidation, they can form carboxylic acids (R-COOH). Determine the intermediate and final products for CH3CH2CH2OH.
Step 4: For parts b and c, examine the provided images to identify the type of alcohol (primary, secondary, or tertiary). Secondary alcohols oxidize to ketones (R-CO-R'), while tertiary alcohols generally do not undergo oxidation under normal conditions because they lack a hydrogen atom on the carbon bonded to the -OH group.
Step 5: Write the balanced chemical equations for the oxidation reactions of each alcohol, showing the reactants, products, and any required oxidizing agents (e.g., [O] or KMnO4). Ensure the equations reflect the correct products based on the type of alcohol.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation of Alcohols
Oxidation of alcohols involves the conversion of alcohols into carbonyl compounds, such as aldehydes or ketones, and ultimately to carboxylic acids, depending on the type of alcohol and the oxidizing agent used. Primary alcohols typically oxidize to aldehydes, while secondary alcohols convert to ketones. Tertiary alcohols, however, do not oxidize easily due to the lack of a hydrogen atom on the carbon bearing the hydroxyl group.
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Types of Alcohols
Alcohols are classified into three categories: primary, secondary, and tertiary, based on the number of carbon atoms attached to the carbon bearing the hydroxyl (-OH) group. Primary alcohols have one carbon attached, secondary alcohols have two, and tertiary alcohols have three. This classification is crucial for predicting the products of oxidation reactions, as the structure influences the oxidation pathway and final products.
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Oxidizing Agents
Oxidizing agents are substances that facilitate the oxidation of other compounds by accepting electrons. Common oxidizing agents for alcohols include potassium dichromate (K2Cr2O7) and chromium trioxide (CrO3), which can convert alcohols into their corresponding carbonyl compounds. The choice of oxidizing agent can affect the reaction conditions and the specific products formed during the oxidation process.
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Related Practice
Textbook Question
From what alcohols might the following carbonyl-containing products have been made (red = O, reddish-brown = Br)?
(a) <IMAGE>
(b) <IMAGE>
Textbook Question
What alcohols yield the following alkenes as the major product on dehydration?
b.
Textbook Question
What alkenes might be formed by dehydration of the following alcohols? If more than one product is possible in a given case, indicate which is major.
b.
Textbook Question
For each of the following molecules, (i) redraw using line structure format, (ii) identify its hydrophobic and hydrophilic parts, and (iii) predict its solubility in water.
c.
Textbook Question
Name the following compounds:
a.
b.