Domanda del libro di testo
What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones? b. 2-octanone
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Ch. 17 - Reactions at the Alpha-Carbon
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
Capitolo 17, Problema 39a,b
What alkyl bromide(s) should be used in the malonic ester synthesis of each of the following carboxylic acids?
a. propanoic acid
b. 2-methylpropanoic acid
Guida verificata passo dopo passo1
Step 1: Understand the malonic ester synthesis. This reaction involves the alkylation of a malonic ester (diethyl malonate) followed by hydrolysis and decarboxylation to produce a carboxylic acid. The key step is the alkylation, where an alkyl halide reacts with the enolate of the malonic ester.
Step 2: For part (a), propanoic acid (CH₃CH₂COOH), identify the alkyl group that needs to be added to the malonic ester. The target carboxylic acid has a three-carbon chain, so the alkyl group to be added is ethyl (CH₃CH₂). The corresponding alkyl bromide is ethyl bromide (CH₃CH₂Br).
Step 3: For part (b), 2-methylpropanoic acid ((CH₃)₂CHCOOH), identify the alkyl group that needs to be added to the malonic ester. The target carboxylic acid has a branched chain with a methyl group at the second carbon. The alkyl group to be added is isopropyl (CH₃)₂CH. The corresponding alkyl bromide is isopropyl bromide ((CH₃)₂CHBr).
Step 4: Write the general reaction for the malonic ester synthesis. The malonic ester (CH₂(CO₂Et)₂) is deprotonated with a base (e.g., NaOEt) to form the enolate ion. This enolate ion reacts with the alkyl bromide (RBr) in an SN2 reaction to form the alkylated malonic ester.
Step 5: After alkylation, the alkylated malonic ester undergoes hydrolysis (with aqueous acid) to form a dicarboxylic acid, followed by decarboxylation (heating) to yield the desired carboxylic acid. Ensure the chosen alkyl bromide matches the structure of the target carboxylic acid.
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Malonic Ester Synthesis
Malonic ester synthesis is a method for synthesizing carboxylic acids through the alkylation of malonic ester followed by hydrolysis and decarboxylation. This reaction typically involves the use of a strong base to deprotonate the malonic ester, allowing it to act as a nucleophile and react with an alkyl halide. The choice of alkyl halide is crucial as it determines the structure of the final carboxylic acid product.
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Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis Concept 1
Alkyl Bromides
Alkyl bromides are organic compounds containing a bromine atom attached to an alkyl group. They are commonly used as electrophiles in nucleophilic substitution reactions, making them suitable for the malonic ester synthesis. The structure of the alkyl bromide influences the final product, so selecting the correct alkyl bromide is essential for achieving the desired carboxylic acid.
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Carboxylic Acid Structure
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). The structure of the target carboxylic acid dictates the required alkyl bromide in the malonic ester synthesis. Understanding the relationship between the carboxylic acid's carbon chain length and branching is vital for determining the appropriate alkyl bromide to use in the synthesis process.
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