Textbook Question
Write a balanced equation for each reaction, showing the major product you expect.
(b)
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Ch. 7 - Structure and Synthesis of Alkenes; Elimination
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 7, Problem 54c
Write a balanced equation for each reaction, showing the major product you expect.
(c) 
Verified step by step guidance1
Step 1: Analyze the reactant structure. The molecule is a cyclohexane ring with two hydroxyl (-OH) groups attached to adjacent carbons. This is a diol (vicinal diol).
Step 2: Recognize the reaction conditions. The presence of concentrated sulfuric acid (H₂SO₄) and heat suggests a dehydration reaction, where water molecules are eliminated.
Step 3: Understand the mechanism. Under acidic conditions, one hydroxyl group is protonated, forming a good leaving group (water). The adjacent hydroxyl group can then lose a proton, leading to the formation of a carbocation intermediate.
Step 4: Predict the major product. The carbocation intermediate undergoes rearrangement or stabilization, followed by elimination of a proton from a neighboring carbon to form a double bond. This results in the formation of an alkene. In this case, the major product is likely cyclohexene.
Step 5: Write the balanced equation. The reaction eliminates two molecules of water (H₂O) from the diol, forming cyclohexene as the major product. The balanced equation is: .
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dehydration Reaction
A dehydration reaction involves the removal of water (H2O) from a molecule, often resulting in the formation of a double bond or a ring structure. In organic chemistry, this process is commonly facilitated by heat and an acid catalyst, such as sulfuric acid, which helps to protonate the hydroxyl groups, making them better leaving groups.
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General Reaction of Dehydration with POCl3
Acid-Catalyzed Reactions
Acid-catalyzed reactions utilize an acid to increase the rate of a chemical reaction. In the context of dehydration, sulfuric acid donates protons to the hydroxyl groups, enhancing their ability to leave as water. This mechanism is crucial for driving the reaction forward and achieving the desired product.
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Major Product Formation
In organic reactions, the major product is the most stable or predominant product formed under the given reaction conditions. Factors such as sterics, electronics, and the stability of intermediates influence which product is favored. Understanding these factors is essential for predicting the outcome of the dehydration reaction shown in the question.
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04:28Predict the MAJOR product.
Related Practice
Textbook Question
Write a balanced equation for each reaction, showing the major product you expect.
(d)
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Textbook Question
Write a balanced equation for each reaction, showing the major product you expect.
(a)
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Textbook Question
Predict the products of the following reactions. When more than one product is expected, predict which will be the major product.
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Textbook Question
Predict the dehydrohalogenation product(s) that result when the following alkyl halides are heated in alcoholic KOH. When more than one product is formed, predict the major and minor products.
(a)
(b)
(c)
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1
rank
Textbook Question
Predict the dehydrohalogenation product(s) that result when the following alkyl halides are heated in alcoholic KOH. When more than one product is formed, predict the major and minor products.
(d)
(e)
1501
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