Textbook Question
Predict the product of the following Lewis acid–Lewis base reactions.
(c)
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Ch. 4 - Acids and Bases: Electron Flow
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 3, Problem 69
Amino acids exist predominantly in one of the following forms. Which is it? Explain your answer.
Verified step by step guidance1
Amino acids are amphoteric molecules, meaning they can act as both acids and bases. This property arises due to the presence of an amino group (-NH2) and a carboxylic acid group (-COOH) in their structure.
In aqueous solutions, amino acids predominantly exist in their zwitterionic form. A zwitterion is a molecule that has both positive and negative charges but is overall electrically neutral.
The zwitterionic form occurs because the amino group (-NH2) is protonated to form -NH3⁺, and the carboxylic acid group (-COOH) is deprotonated to form -COO⁻. This happens at a pH close to the isoelectric point of the amino acid.
The structure on the right in the image represents the zwitterionic form of the amino acid, where the amino group is positively charged (H3N⁺) and the carboxyl group is negatively charged (COO⁻). This is the predominant form of amino acids in physiological conditions (around pH 7).
The structure on the left represents the non-ionized form of the amino acid, which is less common in aqueous solutions. It is typically observed in non-polar solvents or under specific conditions where the pH is far from the isoelectric point.
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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 that serve as the building blocks of proteins. Each amino acid has a central carbon atom bonded to an amino group (-NH2), a carboxyl group (-COOH), a hydrogen atom, and a variable side chain (R group) that determines its unique properties. The structure is crucial for understanding how amino acids interact and form proteins.
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Charged Amino Acids
Zwitterion Form
Amino acids predominantly exist in a zwitterionic form at physiological pH, where the amino group is protonated (-NH3+) and the carboxyl group is deprotonated (-COO-). This dual charge allows amino acids to be soluble in water and participate in biochemical reactions, making it essential to recognize this form when discussing their behavior in biological systems.
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pH and Ionization
The ionization state of amino acids is influenced by the pH of the environment. At different pH levels, the amino and carboxyl groups can gain or lose protons, affecting the overall charge of the amino acid. Understanding the relationship between pH and the ionization of amino acids is vital for predicting their behavior in various biological contexts.
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Related Practice
Textbook Question
Suggest a scheme by which N-methylmorpholine, salicylic acid, and naphthalene can be separated.
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Textbook Question
Using pKa values for the conjugate acids of the bases on each side of the reaction arrow, identify which side of the equilibrium would be favored in the following hypothetical reactions.
(c)
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Textbook Question
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(f)
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Textbook Question
A medicinal chemist needed to deprotonate acetylene ( HC≡CH ) for use in a coupling reaction. Among the options given, which base(s) could be used for this process?
1100
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Textbook Question
Using pKa values for the conjugate acids of the bases on each side of the reaction arrow, identify which side of the equilibrium would be favored in the following hypothetical reactions.
(a)
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