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
2
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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 30b
Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessary reagents.
(b) 
Verified step by step guidance1
Step 1: Analyze the starting material. The given compound is isobutyric acid (2-methylpropanoic acid), which contains a carboxylic acid functional group. This will serve as the precursor for the amino acid synthesis.
Step 2: Convert the carboxylic acid group into an α-bromo acid. Use bromine (Br2) and phosphorus tribromide (PBr3) in the presence of a solvent like acetic acid to perform the Hell-Volhard-Zelinsky reaction. This introduces a bromine atom at the α-carbon adjacent to the carboxylic acid group.
Step 3: Replace the bromine atom with an amino group (-NH2). Treat the α-bromo acid with excess ammonia (NH3) in a solvent like ethanol or water. This substitution reaction yields the corresponding α-amino acid.
Step 4: Purify the product. The resulting compound is an amino acid, specifically valine, which has both an amino group and a carboxylic acid group. Purify the product using recrystallization or other appropriate techniques.
Step 5: Verify the structure of the synthesized amino acid. Use spectroscopic methods such as NMR (nuclear magnetic resonance) and IR (infrared spectroscopy) to confirm the presence of the amino group and carboxylic acid group, ensuring the synthesis was successful.
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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 side chain (R group). The R group determines the specific properties and identity of the amino acid, influencing its role in protein synthesis and function.
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11:14
Charged Amino Acids
Synthesis of Amino Acids
The synthesis of amino acids often involves the formation of the amino and carboxyl functional groups from suitable starting materials. Common methods include the Strecker synthesis, which uses aldehydes, ammonium chloride, and cyanide, and the Gabriel synthesis, which employs phthalimide and alkyl halides to introduce the amino group.
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1:16Synthesis of Amino Acids: Strecker Synthesis Example 1
Reagents in Organic Synthesis
Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. In amino acid synthesis, reagents such as acids, bases, and coupling agents are crucial for forming peptide bonds and modifying functional groups, enabling the construction of the amino acid structure from simpler precursors.
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1:16Synthesis of Amino Acids: Strecker Synthesis Example 1
Related Practice
Textbook Question
Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessary reagents.
(c)
Textbook Question
Predict the products of the following reactions.
(h) product from part (g) + excess NH3 →
2
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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)
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
2
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Textbook Question
Predict the products of the following reactions.
(g) 4-methylpentanoic acid + Br2/PBr3 →
1
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