Domanda del libro di testo
Show how each of the following compounds could be prepared from the given starting material. Each requires a protecting group.
b.
817
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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 46c
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 46cCapitolo 16, Problema 46c
Show how each of the following compounds could be prepared from the given starting material. Each requires a protecting group.
c. 
Guida verificata passo dopo passo1
Step 1: Analyze the transformation. The starting material is a brominated aromatic ketone, and the target compound is a carboxylic acid substituted aromatic ketone. This indicates that the bromine group needs to be replaced with a carboxylic acid group.
Step 2: Introduce a protecting group for the ketone functionality. Ketones are susceptible to side reactions during certain transformations, so protecting the ketone group is necessary. Use ethylene glycol in the presence of an acid catalyst to form a cyclic ketal protecting group.
Step 3: Perform the carboxylation reaction. Replace the bromine atom with a carboxylic acid group using a Grignard reagent. First, convert the bromine into a magnesium bromide Grignard reagent by reacting with magnesium in dry ether. Then, react the Grignard reagent with carbon dioxide (CO₂) to form the carboxylic acid group.
Step 4: Remove the protecting group. Hydrolyze the cyclic ketal under acidic conditions to regenerate the ketone functionality.
Step 5: Purify the product. Use techniques such as recrystallization or chromatography to isolate the desired carboxylic acid substituted aromatic ketone.
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Protecting Groups
Protecting groups are temporary modifications used in organic synthesis to prevent certain functional groups from reacting during a chemical reaction. They allow for selective reactions to occur on other parts of the molecule without interference. After the desired reaction is completed, the protecting group can be removed to restore the original functional group.
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Protecting Groups
Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This reaction is crucial for modifying aromatic compounds, such as bromobenzene, to introduce new functional groups. Understanding the mechanism of EAS helps in predicting the outcomes of reactions involving aromatic compounds.
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03:07EAS Review
Carboxylic Acids
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are important functional groups in organic chemistry, often involved in various reactions, including oxidation and substitution. The conversion of bromobenzene to benzoic acid illustrates the transformation of an aromatic halide into a carboxylic acid, showcasing the utility of functional group interconversions in synthesis.
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04:20Carboxylic Acids Nomenclature
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