Textbook Question
Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:
a. CH3CH2CH2SCH2CH3
1
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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 13
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 13Chapter 11, Problem 13
Which of the following alcohols dehydrates the fastest when heated with acid?
Verified step by step guidance1
Step 1: Understand the dehydration reaction mechanism. Alcohols dehydrate in the presence of acid to form alkenes. The rate of dehydration depends on the stability of the carbocation intermediate formed during the reaction.
Step 2: Analyze the structures of the alcohols provided. Look for the position of the hydroxyl (-OH) group and the substituents attached to the carbon atom bearing the hydroxyl group.
Step 3: Consider the stability of the carbocation intermediate. Tertiary carbocations are more stable than secondary carbocations, which are more stable than primary carbocations. Additionally, resonance stabilization or hyperconjugation can further stabilize the carbocation.
Step 4: Evaluate each alcohol: (A) forms a secondary carbocation, (B) forms a tertiary carbocation, (C) forms a primary carbocation, and (D) forms a tertiary carbocation with resonance stabilization due to the double bond in the ring.
Step 5: Conclude that the alcohol which forms the most stable carbocation (tertiary with resonance stabilization) will dehydrate the fastest. Based on this analysis, identify the alcohol that meets this criterion.
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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. This process often leads to the formation of alkenes. The rate of dehydration can vary significantly based on the structure of the alcohol, with tertiary alcohols generally dehydrating faster than secondary or primary alcohols due to greater carbocation stability.
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Carbocation Stability
Carbocation stability is a key factor in determining the rate of dehydration reactions. Tertiary carbocations are more stable than secondary and primary ones because they are stabilized by the inductive effect of adjacent alkyl groups. The more stable the carbocation formed during dehydration, the faster the reaction will proceed, making the structure of the alcohol crucial in predicting the reaction rate.
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Acid Catalysis
Acid catalysis involves the use of an acid to increase the rate of a chemical reaction. In the dehydration of alcohols, the acid protonates the hydroxyl group, making it a better leaving group. This step is essential for the formation of the carbocation intermediate, which is a critical part of the dehydration mechanism, thus influencing the overall reaction speed.
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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:
b.
Textbook Question
What stereoisomers do the following reactions form?
d.
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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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Textbook Question
What is the major product obtained when each of the following alcohols is heated in the presence of H2SO4?
a.
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