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 9b
What alcohols yield the following alkenes as the major product on dehydration?
b. 
Verified step by step guidance1
Step 1: Understand the dehydration reaction. Dehydration of alcohols involves the removal of a water molecule (H₂O) to form an alkene. This reaction typically occurs in the presence of an acid catalyst, such as H₂SO₄ or H₃PO₄, and heat.
Step 2: Analyze the given alkene structure. Identify the carbon atoms involved in the double bond and their substituents. This will help determine the possible alcohol precursor(s).
Step 3: Recall the mechanism of alcohol dehydration. The reaction proceeds via the E1 or E2 mechanism, depending on the type of alcohol (primary, secondary, or tertiary). For secondary and tertiary alcohols, the E1 mechanism is more common and involves the formation of a carbocation intermediate.
Step 4: Work backward from the alkene. To determine the alcohol precursor, add an -OH group to one of the carbon atoms in the double bond. Consider all possible positions for the -OH group that would lead to the given alkene as the major product. Keep in mind Zaitsev's rule, which states that the more substituted alkene is usually the major product.
Step 5: Verify the structure of the alcohol(s). Ensure that the proposed alcohol(s) can undergo dehydration to yield the given alkene. Consider the stability of the carbocation intermediate (if applicable) and the regioselectivity of the reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dehydration of Alcohols
Dehydration of alcohols is a chemical reaction where an alcohol loses a water molecule, resulting in the formation of an alkene. This process typically occurs under acidic conditions and involves the protonation of the alcohol, followed by the elimination of water. Understanding this mechanism is crucial for predicting the products formed during the reaction.
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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 are more stable due to greater substitution. Recognizing this rule is essential for determining which alkene will be predominant in a given dehydration scenario.
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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 alcohol dehydration, regioselectivity helps identify which alkene is formed based on the structure of the starting alcohol. This concept is vital for understanding how different alcohols can lead to different alkene products during dehydration.
Related Practice
Textbook Question
What products would you expect from oxidation of the following alcohols?
a. CH3CH2CH2OH
b.
c.
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 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
Rank the following according to boiling point, highest to lowest:
a. CH3CH2CH2OH
b. CH3CH2(OH)CH2OH
c. CH3CH2CH3
d. CH2(OH)CH(OH)CH2OH