Textbook Question
Show how you would convert alanine to the following derivatives. Show the structure of the product in each case.
(c) N-benzyloxycarbonyl alanine
(d) tert-butyloxycarbonyl alanine
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Ch. 24 - Amino Acids, Peptides, and Proteins
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 24, Problem 30c
Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessary reagents.
(c) 
Verified step by step guidance1
Identify the target amino acid you wish to synthesize. For example, if the target is alanine, note its structure: CH3-CH(NH2)-COOH. This will help you determine the functional groups and carbon skeleton required.
Choose an appropriate starting material. A common starting material for amino acid synthesis is an α-halo acid (e.g., a compound like CH3-CH(Cl)-COOH for alanine). Alternatively, you can use a simpler compound like an aldehyde or ketone, depending on the synthesis route.
Plan the introduction of the amino group (-NH2). A common method is to use the Gabriel synthesis or reductive amination. For example, if starting with an α-halo acid, you can replace the halogen with an amine group using reagents like NH3 (ammonia).
Ensure the carboxylic acid group (-COOH) is present or can be introduced. If starting with an aldehyde or ketone, you can use the Strecker synthesis, which involves reacting the compound with NH3 and HCN to form an aminonitrile, followed by hydrolysis to yield the amino acid.
Verify the stereochemistry of the product. Many amino acids are chiral, so you may need to use specific reagents or conditions to ensure the correct enantiomer is formed. For example, enzymatic resolution or chiral catalysts can be used to obtain the desired stereoisomer.
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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 a central carbon atom bonded to an amino group (-NH2), a carboxyl group (-COOH), a hydrogen atom, and a variable R group (side chain). The R group determines the specific properties and identity of each amino acid, influencing its role in protein synthesis and function.
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Charged Amino Acids
Synthetic Pathways
The synthesis of amino acids can be achieved through various chemical pathways, including the Strecker synthesis and Gabriel synthesis. These methods involve specific reagents and conditions to construct the amino acid's backbone and functional groups, allowing for the transformation of simple starting materials into complex amino acids.
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Reagents and Reaction Conditions
Understanding the appropriate reagents and reaction conditions is crucial for synthesizing amino acids. Common reagents include alkyl halides, amines, and carbonyl compounds, while reaction conditions such as temperature, pH, and solvent choice can significantly affect the yield and purity of the desired amino acid product.
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Related Practice
Textbook Question
Predict the products of the following reactions.
(h) product from part (g) + excess NH3 →
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Textbook Question
Suggest a method for the synthesis of the unnatural D enantiomer of alanine from the readily available L enantiomer of lactic acid.
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Textbook Question
Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessary reagents.
(a)
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Textbook Question
Show how you would convert alanine to the following derivatives. Show the structure of the product in each case.
(a) alanine isopropyl ester
(b) N-benzoylalanine
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Textbook Question
Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessary reagents.
(b)
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