Textbook Question
Draw the products of the following reactions:
c.
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Ch. 17 - Reactions at the Alpha-Carbon
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- 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
Chapter 18, Problem 74a
Show how the amino acid alanine can be synthesized from propanoic acid.
Verified step by step guidance1
Identify the structure of alanine and propanoic acid. Alanine is an amino acid with the structure CH₃-CH(NH₂)-COOH, and propanoic acid is CH₃-CH₂-COOH.
Recognize that the transformation involves introducing an amino group (-NH₂) at the alpha-carbon of propanoic acid. This is a common reaction in amino acid synthesis.
Convert propanoic acid into an alpha-bromo acid. This can be achieved by brominating the alpha-carbon using bromine (Br₂) in the presence of phosphorus tribromide (PBr₃) to form 2-bromopropanoic acid (CH₃-CH(Br)-COOH).
Substitute the bromine atom with an amino group. This can be done by treating 2-bromopropanoic acid with excess ammonia (NH₃), resulting in the formation of alanine (CH₃-CH(NH₂)-COOH).
Purify the product to isolate alanine. This can involve recrystallization or other purification techniques to ensure the final product is pure.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Amino Acid Structure
Amino acids are organic compounds characterized by the presence of an amino group (-NH2), a carboxyl group (-COOH), and a unique side chain (R group) that determines their properties. Alanine, specifically, has a simple side chain consisting of a methyl group (-CH3), making it a non-polar, aliphatic amino acid. Understanding this structure is essential for grasping how alanine can be synthesized from simpler organic molecules.
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Decarboxylation
Decarboxylation is a chemical reaction that involves the removal of a carboxyl group (-COOH) from a molecule, releasing carbon dioxide (CO2). In the synthesis of alanine from propanoic acid, decarboxylation plays a crucial role as it transforms the propanoic acid into an intermediate that can be further modified to form alanine. This process is fundamental in organic synthesis and metabolic pathways.
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Transamination
Transamination is a biochemical process where an amino group from one amino acid is transferred to a keto acid, forming a new amino acid and a new keto acid. In the context of synthesizing alanine from propanoic acid, transamination can occur with an intermediate compound, allowing the incorporation of the amino group necessary for alanine formation. This concept is vital for understanding amino acid metabolism and synthesis.
Related Practice
Textbook Question
Show how the following compound can be prepared from starting materials that have no more than five carbons:
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Textbook Question
Show how the following compounds can be synthesized. The only carbon-containing compounds available to you for each synthesis are shown.
b.
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Textbook Question
A Mannich reaction puts a -group on the α-carbon of a ketone. Propose a mechanism for the reaction.
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Textbook Question
Draw the products of the following reactions:
d.
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Textbook Question
A student tried to prepare the following compounds using aldol condensations. Which of these compounds was she successful in synthesizing? Explain why the other syntheses were not successful.
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