Domanda del libro di testo
Excess ammonia must be used when a primary amine is synthesized by reductive amination. What product will be obtained if the reaction is carried out with excess carbonyl compound?
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
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
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Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 35a
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 35aCapitolo 16, Problema 35a
The compounds commonly known as 'amino acids' are actually α-aminocarboxylic-aminocarboxylic acids. What carbonyl compounds should be used to synthesize the two amino acids shown here?
a. 
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Step 1: Identify the amino acid structure shown in the image. The compound has an amino group (-NH2), a carboxylate group (-COO⁻), and a side chain containing an isopropyl group. This structure corresponds to leucine, an α-amino acid.
Step 2: Recall the Strecker synthesis method for amino acids. This method involves the reaction of an aldehyde with ammonia (NH3) and hydrogen cyanide (HCN) to form an α-aminonitrile, which is then hydrolyzed to yield the amino acid.
Step 3: Determine the aldehyde required for the synthesis of leucine. The side chain of leucine (isopropyl group) suggests that the aldehyde should be isobutyraldehyde (CH3CH(CH3)CHO). This aldehyde provides the correct carbon skeleton for leucine.
Step 4: Write the reaction sequence. In the Strecker synthesis, isobutyraldehyde reacts with ammonia and hydrogen cyanide to form an α-aminonitrile intermediate. This intermediate is then hydrolyzed under acidic conditions to produce leucine.
Step 5: Summarize the process. To synthesize leucine, the carbonyl compound is isobutyraldehyde. This compound undergoes the Strecker synthesis pathway to yield the desired amino acid.
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Amino Acids
Amino acids are organic compounds that serve as the building blocks of proteins. They contain both an amino group (-NH2) and a carboxylic acid group (-COOH), making them α-aminocarboxylic acids. The structure of amino acids allows them to participate in various biochemical reactions, including the formation of peptide bonds, which link them together to form proteins.
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Standard Amino Acids
Reductive Amination
Reductive amination is a chemical reaction that involves the conversion of a carbonyl compound (such as an aldehyde or ketone) into an amine. This process typically involves the formation of an imine intermediate, which is then reduced to yield the amine. In the context of amino acid synthesis, this reaction is crucial for introducing the amino group into the carbon skeleton derived from the carbonyl compound.
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07:12Reductive Amination
Carbonyl Compounds
Carbonyl compounds are organic molecules that contain a carbonyl group (C=O), which can be found in aldehydes, ketones, carboxylic acids, and esters. In the synthesis of amino acids, specific carbonyl compounds are selected based on their ability to react with amines through reductive amination, ultimately leading to the formation of the desired amino acid structure.
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01:40Defining meso compounds.
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The compounds commonly known as 'amino acids' are actually α-aminocarboxylic-aminocarboxylic acids. What carbonyl compounds should be used to synthesize the two amino acids shown here?
b.
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