Textbook Question
When heated with H2SO4, both 3,3-dimethyl-2-butanol and 2,3-dimethyl-2-butanol are dehydrated to form 2,3-dimethyl-2-butene. Which alcohol dehydrates more rapidly?
2
views
Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 60c
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 60cChapter 11, Problem 60c
What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?
c. 0.1MNaOH
Verified step by step guidance1
Identify the structure of 2-ethyloxirane. It is an epoxide (a three-membered cyclic ether) with an ethyl group attached to one of the carbons in the ring.
Understand the reactivity of epoxides in the presence of a base like NaOH. Epoxides are highly strained and reactive, and bases can open the ring via a nucleophilic attack.
Determine the site of nucleophilic attack. In basic conditions, the nucleophile (OH⁻) will attack the less substituted carbon of the epoxide due to steric hindrance and electronic effects.
Write the mechanism for the reaction. The OH⁻ attacks the less substituted carbon of the epoxide, breaking the C-O bond and opening the ring. This results in the formation of a diol (a molecule with two hydroxyl groups).
Assign the stereochemistry of the product. The nucleophilic attack occurs with inversion of configuration at the carbon being attacked, while the other carbon retains its configuration. Ensure the final product reflects this stereochemical outcome.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
3mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Epoxide Reactivity
Epoxides, or oxiranes, are three-membered cyclic ethers that are highly reactive due to the strain in their ring structure. This strain makes them susceptible to nucleophilic attack, which can lead to ring-opening reactions. Understanding how epoxides react with nucleophiles is crucial for predicting the products of reactions involving them.
Recommended video:
Guided course
02:19
General properties of epoxidation.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the case of epoxides, a nucleophile such as hydroxide ion (OH-) can attack the less hindered carbon atom of the epoxide, leading to the opening of the ring and the formation of an alcohol. This concept is essential for determining the major product of the reaction.
Recommended video:
Guided course
01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to occur at one site over another in a molecule. In the context of epoxide reactions, the regioselectivity is influenced by steric and electronic factors, which dictate which carbon atom in the epoxide is attacked by the nucleophile. Understanding regioselectivity helps in predicting the specific product formed when 2-ethyloxirane reacts with NaOH.
Recommended video:
Guided course
05:09Heck Reaction
Related Practice
Textbook Question
What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?
a. 0.1MHCl
b. CH3OH/HCl
1
views
Textbook Question
Starting with (R)-1-deuterio-1-propanol, how could you prepare
c. (R)-1-deuterio-1-methoxypropane?
2
views
Textbook Question
What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?
d. CH3OH/CH3O-
1
views
Textbook Question
Write the appropriate reagent over each arrow.
1
views
Textbook Question
Write the appropriate reagent over each arrow.
1
views