Textbook Question
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(d)
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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 66e
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(e) 
Verified step by step guidance1
Analyze the structure of the molecule: The molecule contains a benzene ring with two hydroxyl (-OH) groups in the ortho position and a nitro group (-NO2) attached to the ring.
Identify the acidic protons: The hydroxyl groups (-OH) are acidic due to the ability of the oxygen atom to donate a proton. The nitro group is electron-withdrawing, which increases the acidity of the hydroxyl groups by stabilizing the negative charge on the conjugate base.
Determine the effect of a strong base: A strong base will deprotonate one of the hydroxyl groups, forming a phenoxide ion (-O⁻). The base will preferentially deprotonate the more acidic hydroxyl group, which is influenced by the electron-withdrawing nitro group.
Predict the product: The reaction will result in the formation of a phenoxide ion at the position of the deprotonated hydroxyl group. The nitro group will remain unchanged, and the other hydroxyl group will remain protonated.
Consider resonance stabilization: The phenoxide ion formed will be stabilized by resonance, where the negative charge on the oxygen can delocalize into the aromatic ring. The nitro group further stabilizes the resonance structure by withdrawing electron density.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Strong Bases
Strong bases are substances that can completely dissociate in solution to produce hydroxide ions (OH-). Common examples include sodium hydroxide (NaOH) and potassium hydroxide (KOH). In organic chemistry, strong bases are often used to deprotonate acidic functional groups, leading to the formation of reactive intermediates such as alkoxides or carbanions.
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Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) from an acid to a base. In the context of organic molecules, hydroxyl groups (-OH) can act as weak acids, donating a proton to a strong base. This reaction can lead to the formation of alkoxide ions, which are important in various organic reactions, including nucleophilic substitutions and eliminations.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the provided structure, the hydroxyl (-OH) and amine (-NH) groups are functional groups that can participate in acid-base reactions. Understanding the reactivity of these groups is crucial for predicting the products of reactions involving strong bases.
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Related Practice
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For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(c)
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Suggest a scheme by which N-methylmorpholine, salicylic acid, and naphthalene can be separated.
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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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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?
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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.
(b)
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