Domanda del libro di testo
An alternate method for the synthesis of alkynes relies on the double elimination of H―Br from a dihaloalkane under basic conditions. Suggest a mechanism for this reaction that we discuss in Chapter 12.
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Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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TOC.tableOfContents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases/Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo
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Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblema 62
Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblema 62Capitolo 9, Problema 62
Ethinylestradiol is a synthetic hormone mimic used as a contraceptive for its ability to prevent ovulation. Suggest a mechanism for the synthesis using sodium acetylide and estrone, followed by quenching with acid.
Guida verificata passo dopo passo1
Step 1: Recognize the key reactants and their roles. Estrone is a ketone-containing compound, and sodium acetylide (NaC≡CH) is a strong nucleophile due to the negatively charged acetylide ion. The acetylide ion can attack electrophilic centers, such as the carbonyl group in estrone.
Step 2: Identify the first step of the mechanism. The acetylide ion will perform a nucleophilic attack on the carbonyl carbon of estrone. This occurs because the carbonyl carbon is electrophilic due to the partial positive charge created by the oxygen atom's electronegativity. Represent this step as: Estrone + NaC≡CH → Intermediate (alkoxide).
Step 3: Describe the formation of the intermediate. The nucleophilic attack results in the formation of an alkoxide intermediate, where the oxygen atom from the carbonyl group now carries a negative charge. This intermediate is stabilized by resonance within the molecule.
Step 4: Explain the quenching step. The alkoxide intermediate is quenched with acid (e.g., HCl or H₂SO₄), which protonates the negatively charged oxygen atom, converting it into a hydroxyl group. This step completes the synthesis of the desired product.
Step 5: Highlight the final product. The reaction results in the formation of ethinylestradiol, where the acetylide group has been added to the estrone structure, and the carbonyl group has been converted into a hydroxyl group. This product is a synthetic hormone mimic used in contraceptives.
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Sodium Acetylide as a Nucleophile
Sodium acetylide is a strong nucleophile due to the presence of a negatively charged carbon atom. In organic synthesis, it can attack electrophilic centers, such as carbonyl groups, facilitating the formation of new carbon-carbon bonds. This property is crucial in the synthesis of complex molecules, including hormone mimics like ethinylestradiol.
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03:19
Sodium Alkynide Alkylation
Carbonyl Chemistry
Carbonyl compounds, such as ketones and aldehydes, are characterized by a carbon-oxygen double bond. They are key intermediates in organic reactions, particularly in nucleophilic addition reactions. Understanding how nucleophiles like sodium acetylide interact with carbonyl groups is essential for proposing a synthesis mechanism involving estrone.
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04:20Carboxylic Acids Nomenclature
Quenching with Acid
Quenching with acid is a common step in organic synthesis that involves adding an acid to neutralize a reaction mixture, often to protonate reactive intermediates. This step can stabilize the product and facilitate the removal of byproducts. In the context of synthesizing ethinylestradiol, acid quenching would help finalize the reaction and yield the desired hormone mimic.
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02:23Using factors affecting acidity to rank acids
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Domanda del libro di testo
In 1973, Caine and Tuller reported a synthesis of racemic oplapanone, a sesquiterpene isolated from Oplopanax japonicus (a deciduous shrub) involving a reaction we learned in this chapter. Predict the product of the reaction shown. (Caine, D.; Tuller, F. N. J. Org. Chem. 1973, 38, 3663.)
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Domanda del libro di testo
A chemist attempted to do the following acetylide alkylation reaction but was unsuccessful in several attempts, producing only the original starting materials in each case. Explain why the reaction didn't work.
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