Textbook Question
Which of the following alcohols dehydrates the fastest when heated with acid?
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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 14a
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 14aChapter 11, Problem 14a
What is the major product obtained when each of the following alcohols is heated in the presence of H2SO4?
a. 
Verified step by step guidance1
Step 1: Recognize the reaction type. Heating an alcohol in the presence of H2SO4 typically leads to an elimination reaction (E1 mechanism), resulting in the formation of an alkene. The sulfuric acid acts as a catalyst, protonating the alcohol group to form a good leaving group (water).
Step 2: Analyze the structure of the alcohol. The given alcohol is a tertiary alcohol because the carbon attached to the hydroxyl group is connected to three other carbon atoms. Tertiary alcohols undergo elimination reactions readily due to the stability of the carbocation intermediate formed.
Step 3: Protonation of the hydroxyl group. The hydroxyl group (-OH) is protonated by H2SO4, converting it into water (a good leaving group). This step facilitates the departure of the water molecule, leaving behind a tertiary carbocation.
Step 4: Formation of the carbocation intermediate. The tertiary carbocation formed is highly stable due to hyperconjugation and inductive effects from the surrounding alkyl groups. This stability drives the reaction forward.
Step 5: Determine the major product. The elimination of a proton from a β-carbon (adjacent to the carbocation) leads to the formation of the most substituted alkene (following Zaitsev's rule). The major product will be the alkene with the highest degree of substitution, as this is thermodynamically favored.
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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, typically in the presence of an acid catalyst like sulfuric acid (H2SO4). This process often leads to the formation of alkenes, as the elimination of water results in the formation of a double bond between carbon atoms. Understanding this reaction is crucial for predicting the products formed when heating alcohols.
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General Reaction of Dehydration with POCl3
Acid Catalysis
Acid catalysis involves the use of an acid to increase the rate of a chemical reaction. In the dehydration of alcohols, H2SO4 donates protons (H+) to the alcohol, enhancing its electrophilicity and facilitating the loss of water. This concept is essential for understanding how the reaction proceeds and the stability of the intermediates formed during the process.
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Carbocation Stability
Carbocation stability is a key factor in determining the major product of dehydration reactions. More stable carbocations, such as tertiary carbocations, are favored during the reaction because they can better accommodate the positive charge. The stability of the carbocation intermediate influences the pathway of the reaction and the final alkene product formed after dehydration.
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Related Practice
Textbook Question
Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:
a. CH3CH2CH2SCH2CH3
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Textbook Question
Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:
b.
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Textbook Question
Heating an alcohol with sulfuric acid is a good way to prepare a symmetrical ether such as diethyl ether.
b. How would you synthesize ethyl propyl ether?
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Textbook Question
What is the major product obtained when each of the following alcohols is heated in the presence of H2SO4?
b.
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Textbook Question
Heating an alcohol with sulfuric acid is a good way to prepare a symmetrical ether such as diethyl ether.
a. Explain why it is not a good way to prepare an unsymmetrical ether such as ethyl propyl ether.
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