Domanda del libro di testo
Show how you would make the following ethers, using only simple alcohols and any needed reagents as your starting materials.
(a) 1-methoxybutane
(b) 2-ethoxy-2-methylpropane
(c) benzyl cyclopentyl ether
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Ch. 14 - Ethers, Epoxides, and Thioethers
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- 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
Capitolo 14, Problema 33j,k,l
Predict the products of the following reactions.
(j) 
(k) 
(l) 
Guida verificata passo dopo passo1
Step 1 (Reaction j): Analyze the reaction conditions. Phenyl lithium (PhLi) is a strong nucleophile and base. It will attack the electrophilic carbon of the epoxide ring, opening the ring. The acidic workup (H3O+) will protonate the oxygen atom, forming an alcohol.
Step 2 (Reaction j): Determine the regioselectivity of the epoxide ring opening. Under basic conditions, the nucleophile attacks the less substituted carbon of the epoxide due to steric hindrance.
Step 3 (Reaction k): Examine the reaction conditions. mCPBA (meta-chloroperoxybenzoic acid) is a peracid used to convert alkenes into epoxides. The reaction occurs via electrophilic addition to the double bond.
Step 4 (Reaction k): Predict the stereochemistry of the epoxide formation. mCPBA typically forms epoxides with retention of the alkene's stereochemistry, resulting in a syn addition.
Step 5 (Reaction l): Analyze the reaction conditions. HBr reacts with epoxides via an acid-catalyzed ring-opening mechanism. The bromide ion (Br⁻) acts as a nucleophile, attacking the more substituted carbon of the epoxide due to the carbocation-like intermediate formed under acidic conditions.
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Nucleophilic Addition
Nucleophilic addition is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically found in carbonyl compounds. In this case, phenyl lithium (PhLi) acts as a strong nucleophile, attacking the carbonyl carbon of the ketone, leading to the formation of an alkoxide intermediate.
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08:27
Nucleophilic Addition
Reactivity of Organolithium Reagents
Organolithium reagents, such as phenyl lithium, are highly reactive and serve as strong nucleophiles in organic synthesis. They can effectively add to electrophilic centers, such as carbonyl groups, resulting in the formation of new carbon-carbon bonds. Their reactivity is crucial for the transformation of ketones into alcohols after subsequent protonation.
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01:52Reagents
Protonation of Alkoxides
After the nucleophilic addition of phenyl lithium to the carbonyl compound, the resulting alkoxide intermediate is typically protonated to yield the final alcohol product. This step is often facilitated by adding a proton source, such as H3O+, which donates a proton to the negatively charged oxygen, converting the alkoxide into a stable alcohol.
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03:Proton Splitting
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(A true story.) An inexperienced graduate student moved into a laboratory and began work. He needed some diethyl ether for a reaction, so he opened an old, rusty 1-gallon can marked 'ethyl ether' and found there was half a gallon left. To purify the ether, the student set up a distillation apparatus, started a careful distillation, and went to the stockroom for the other reagents he needed. While he was at the stockroom, the student heard a muffled "boom." He quickly returned to his lab to find a worker from another laboratory putting out a fire. Most of the distillation apparatus was embedded in the ceiling.
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Predict the products of the following reactions.
(a) sec-butyl isopropyl ether + concd. HBr, heat
(b) 2-ethoxy-2-methylpentane + concd. HBr, heat
(c) di-n-butyl ether + hot concd. NaOH
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Predict the products of the following reactions.
(g) trans-2,3-epoxyoctane + H+, H2O
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Predict the products of the following reactions.
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