Domanda del libro di testo
Propose a mechanism to explain how dimethyl sulfoxide and oxalyl chloride react to form the dimethylchlorosulfonium ion used as the oxidizing agent in the Swern oxidation.
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 79b
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 79bCapitolo 16, Problema 79b
Draw structures for A-D for each of the following:
b. 
Guida verificata passo dopo passo1
Step 1: Analyze the starting compound, which is a ketone. The first reaction involves LiAlH4 followed by H2O. LiAlH4 is a strong reducing agent that reduces ketones to secondary alcohols. Therefore, Compound i will be the secondary alcohol corresponding to the reduction of the ketone group.
Step 2: The second reaction involves SOCl2 in pyridine. SOCl2 is commonly used to convert alcohols into alkyl chlorides via substitution. Thus, Compound ii will be the alkyl chloride formed from the secondary alcohol in Compound i.
Step 3: The third reaction involves the use of P(C6H5)3 and C4H9Li. This is indicative of a Wittig reaction, where the alkyl chloride (Compound ii) reacts to form a phosphonium ylide intermediate, which then reacts with a carbonyl compound to form an alkene. Compound iii will be the alkene formed.
Step 4: The final step involves the conversion of Compound iii into Compound iv. Based on the structure provided, Compound iv appears to be a ketone. This suggests that Compound iii undergoes oxidation to regenerate the ketone functional group.
Step 5: Draw the structures for each compound (A-D) based on the transformations described above. Ensure that the stereochemistry and connectivity are consistent with the reagents and reaction conditions provided.
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Reduction Reactions
Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In organic chemistry, this often refers to the conversion of carbonyl compounds (like aldehydes and ketones) to alcohols. The reaction shown in the image uses lithium aluminum hydride (LiAlH4), a strong reducing agent, to reduce a carboxylic acid to an alcohol, which is crucial for understanding the transformation of compounds in the reaction scheme.
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07:12
Reductive Amination
Formation of Acid Chlorides
Acid chlorides are derived from carboxylic acids by replacing the hydroxyl (-OH) group with a chlorine atom. This transformation is typically achieved using reagents like thionyl chloride (SOCl2) in the presence of a base such as pyridine. Understanding this conversion is essential for recognizing how the reaction scheme progresses from a carboxylic acid to an acid chloride, which is an important intermediate in organic synthesis.
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03:13Acid Chloride Nomenclature
Grignard Reagents
Grignard reagents are organomagnesium compounds that are highly reactive and used to form carbon-carbon bonds in organic synthesis. They are generated by reacting alkyl or aryl halides with magnesium metal. In the reaction scheme, the use of a Grignard reagent (C4H9Li) indicates a step where the acid chloride is reacted to form a new carbon chain, highlighting the importance of these reagents in building complex organic molecules.
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02:12Carbonation of Grignard Reagents
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Unlike a phosphonium ylide that reacts with an aldehyde or a ketone to form an alkene, a sulfonium ylide reacts with an aldehyde or a ketone to form an epoxide. Explain why one ylide forms an alkene, whereas the other forms an epoxide.
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