Textbook Question
Describe how each of the following compounds could be synthesized from the given starting material.
a.
1175
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 81
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 81Chapter 11, Problem 81
Ethylene oxide reacts readily with HO- because of the strain in the three-membered ring. Explain why cyclopropane, a compound with approximately the same amount of strain, does not react with HO-.
Verified step by step guidance1
Understand the structure and reactivity of ethylene oxide: Ethylene oxide is a three-membered cyclic ether (epoxide) with significant ring strain due to its bond angles being much smaller than the ideal tetrahedral angle of 109.5°. This strain makes the molecule highly reactive, especially toward nucleophiles like HO⁻.
Analyze the reaction mechanism of ethylene oxide with HO⁻: The nucleophile (HO⁻) attacks the electrophilic carbon in the epoxide ring, leading to ring opening. This reaction is facilitated by the partial positive charge on the carbon atoms of the epoxide due to the electronegativity of oxygen.
Compare the structure of cyclopropane: Cyclopropane is a three-membered ring hydrocarbon with similar ring strain due to its compressed bond angles. However, unlike ethylene oxide, cyclopropane lacks an electronegative atom like oxygen, which would create an electrophilic site for nucleophilic attack.
Explain the lack of reactivity of cyclopropane with HO⁻: Cyclopropane is composed of only carbon and hydrogen atoms, which are nonpolar and do not provide an electrophilic site for the nucleophile (HO⁻) to attack. The absence of a polar bond or partial charges in cyclopropane makes it inert to nucleophilic attack under normal conditions.
Conclude the reasoning: The key difference lies in the presence of an electrophilic site in ethylene oxide due to the oxygen atom, which facilitates nucleophilic attack and ring opening. Cyclopropane, despite having similar ring strain, does not have such a site, and therefore does not react with HO⁻.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ring Strain
Ring strain occurs in cyclic compounds when the bond angles deviate from the ideal tetrahedral angle of 109.5 degrees, leading to increased energy and reactivity. In ethylene oxide, the three-membered ring creates significant angle strain, making it more reactive towards nucleophiles like HO-. Cyclopropane also has ring strain, but its stability is enhanced by the ability to adopt a more favorable conformation.
Recommended video:
Guided course
02:46
What is angle strain?
Nucleophilic Attack
Nucleophilic attack involves a nucleophile, such as HO-, attacking an electrophilic center in a molecule. Ethylene oxide's strained ring makes the carbon atoms more electrophilic, facilitating this reaction. In contrast, cyclopropane lacks such electrophilic centers due to its stable structure, making it less susceptible to nucleophilic attack despite having similar strain.
Recommended video:
Guided course
08:27Nucleophilic Addition
Stability of Cyclopropane
Cyclopropane is relatively stable due to its ability to maintain a planar structure, which minimizes torsional strain. This stability results in lower reactivity compared to ethylene oxide, where the strain leads to a higher energy state. Consequently, cyclopropane does not readily undergo reactions with nucleophiles like HO-, as it does not have the same driving force for reaction as ethylene oxide.
Recommended video:
Guided course
03:43The radical stability trend.
Related Practice
Textbook Question
Propose a mechanism for each of the following reactions:
a.
861
views
Textbook Question
When ethyl ether is heated with excess HI for several hours, the only organic product obtained is ethyl iodide. Explain why ethyl alcohol is not obtained as a product.
1291
views
Textbook Question
Propose a mechanism for each of the following reactions:
b.
812
views
Textbook Question
When the following seven-membered ring alcohol is dehydrated, three alkenes are formed. Propose a mechanism for their formation.
1568
views
Textbook Question
How could you synthesize isopropyl propyl ether, using isopropyl alcohol as the only carbon-containing reagent?
1006
views