Textbook Question
Suggest how you would separate the free L-amino acid from its acylated D enantiomer in Figure 24-5.
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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 15
Give equations for the formation and hydrogenolysis of glutamine benzyl ester.
Verified step by step guidance1
Write the structure of glutamine, which is an amino acid with the formula C5H10N2O3. Identify the functional groups: an amine (-NH2), a carboxylic acid (-COOH), and a side chain containing an amide (-CONH2).
To form the benzyl ester of glutamine, react the carboxylic acid group (-COOH) of glutamine with benzyl alcohol (C6H5CH2OH) in the presence of an acid catalyst (e.g., H2SO4) or a coupling agent like DCC (dicyclohexylcarbodiimide). This reaction forms the benzyl ester (-COOCH2C6H5) at the carboxylic acid group.
Write the chemical equation for the esterification reaction: Glutamine + Benzyl alcohol → Glutamine benzyl ester + Water. Use MathML to represent the structures of the reactants and products.
For the hydrogenolysis of glutamine benzyl ester, use a hydrogenation catalyst such as palladium on carbon (Pd/C) under a hydrogen atmosphere (H2). This reaction cleaves the benzyl ester group (-COOCH2C6H5) back to the carboxylic acid (-COOH) and forms toluene (C6H5CH3) as a byproduct.
Write the chemical equation for the hydrogenolysis reaction: Glutamine benzyl ester + H2 → Glutamine + Toluene. Use MathML to represent the structures of the reactants and products.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Formation of Glutamine Benzyl Ester
The formation of glutamine benzyl ester involves the reaction of glutamine, an amino acid, with benzyl alcohol in the presence of an acid catalyst. This process is known as esterification, where the carboxylic acid group of glutamine reacts with the hydroxyl group of benzyl alcohol, resulting in the formation of an ester bond and the release of water.
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Reactions at Benzylic Positions Concept 1
Hydrogenolysis
Hydrogenolysis is a chemical reaction that involves the cleavage of a bond in the presence of hydrogen, typically using a catalyst such as palladium or platinum. In the context of glutamine benzyl ester, hydrogenolysis would break the ester bond, converting the ester back into glutamine and benzyl alcohol. This reaction is important for the selective removal of protecting groups in organic synthesis.
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2:01Reactions of Amino Acids: Hydrogenolysis Concept 1
Esterification and Hydrolysis Reactions
Esterification and hydrolysis are fundamental organic reactions involving the formation and breakdown of esters. Esterification is the process of forming an ester from an alcohol and a carboxylic acid, while hydrolysis is the reverse reaction, where an ester reacts with water to yield an alcohol and a carboxylic acid. Understanding these reactions is crucial for manipulating and synthesizing organic compounds in the laboratory.
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