Textbook Question
What products would you expect from oxidation of the following alcohols?
a. CH3CH2CH2OH
b.
c.
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 8b
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. 
Verified step by step guidance1
Identify the alcohol structure in the given problem. Dehydration of alcohols involves the removal of a water molecule, which typically occurs when the alcohol is heated in the presence of an acid catalyst (e.g., H₂SO₄ or H₃PO₄).
Determine the possible β-hydrogens (hydrogens on the carbon adjacent to the carbon bearing the hydroxyl group) that can be eliminated along with the hydroxyl group (-OH). This will help identify the potential alkenes that can form.
Apply Zaitsev's rule, which states that the major product of an elimination reaction is the more substituted alkene (the one with the greater number of alkyl groups attached to the double-bonded carbons). This will help you predict the major product.
Draw the structures of all possible alkenes that can form by removing a β-hydrogen from different adjacent carbons. Ensure that you account for all possible elimination pathways.
Indicate which alkene is the major product based on Zaitsev's rule. If there are multiple products, clearly label the major and minor products.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dehydration Reaction
Dehydration is a chemical reaction that involves the removal of a water molecule from a compound. In organic chemistry, this often refers to the conversion of alcohols into alkenes by eliminating a hydroxyl group and a hydrogen atom. This reaction typically requires an acid catalyst and can lead to the formation of multiple products depending on the structure of the alcohol.
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Alcohol Reactions: Dehydration Reactions Concept 1
Zaitsev's Rule
Zaitsev's Rule states that in elimination reactions, the more substituted alkene is usually the major product. This principle helps predict the outcome of dehydration reactions by favoring the formation of alkenes that have more alkyl groups attached to the double bond, which results in greater stability due to hyperconjugation and inductive effects.
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1:24Zaitsev’s Rule Concept 2
Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In the context of dehydration of alcohols, regioselectivity determines which alkene is formed based on the stability of the resulting double bond and the position of the substituents, influencing the major product in the reaction.
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
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
Ethers have some slight solubility in water. Explain this using the concept of hydrogen bonding.
Textbook Question
Rank the following according to boiling point, highest to lowest:
a. CH3CH2CH2OH
b. CH3CH2(OH)CH2OH
c. CH3CH2CH3
d. CH2(OH)CH(OH)CH2OH