Textbook Question
Which of the following bases would favorably deprotonate a hydroxyl group?
(d) Et3N
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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
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
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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 21b
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 21bChapter 12, Problem 21b
Which of the following bases would favorably deprotonate a hydroxyl group?
(b) NaOH
Verified step by step guidance1
Understand the concept of deprotonation: Deprotonation is the removal of a proton (H⁺) from a molecule, which in this case is a hydroxyl group (OH). The ability of a base to deprotonate a hydroxyl group depends on its strength.
Identify the hydroxyl group: The hydroxyl group is represented as OH. It is a common functional group in organic chemistry, consisting of an oxygen atom bonded to a hydrogen atom.
Consider the strength of the base: Sodium hydroxide (NaOH) is a strong base. Strong bases are more likely to deprotonate weak acids, such as alcohols, which contain hydroxyl groups.
Evaluate the acidity of the hydroxyl group: Hydroxyl groups in alcohols are weakly acidic. The pKa of a typical alcohol is around 16-18, indicating that it can be deprotonated by a strong base.
Conclude the likelihood of deprotonation: Given that NaOH is a strong base, it can favorably deprotonate a hydroxyl group by removing the hydrogen ion (H⁺), forming water (H₂O) and the corresponding alkoxide ion.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Chemistry
Acid-base chemistry involves the transfer of protons between molecules. A base is a substance that can accept protons, while an acid can donate them. Understanding the strength of acids and bases is crucial for predicting reactions, such as deprotonation, where a base removes a proton from an acid.
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The Lewis definition of acids and bases.
pKa and Basicity
The pKa value of a compound indicates its acidity; lower pKa values mean stronger acids. A base can deprotonate an acid if the base's conjugate acid has a higher pKa than the acid being deprotonated. NaOH is a strong base, capable of deprotonating hydroxyl groups due to its high basicity.
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Hydroxyl Group
A hydroxyl group consists of an oxygen atom bonded to a hydrogen atom (-OH). It is a common functional group in organic chemistry, found in alcohols. The ability of a base to deprotonate a hydroxyl group depends on the base's strength and the acidity of the hydroxyl group.
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Related Practice
Textbook Question
The intended SN2 displacement of the 1° chloride by acetylide is unsuccessful for the molecule below. Why?
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Textbook Question
Which of the following bases would favorably deprotonate a hydroxyl group?
(a)
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Textbook Question
In contrast to the results of Assessment 13.18, when a secondary haloalkane is treated with sodium ethanethiolate, we predict formation of a thioether. How is this rationalized?
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Textbook Question
Which of the following bases would favorably deprotonate a hydroxyl group?
(e)
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Textbook Question
Which of the following bases would favorably deprotonate a hydroxyl group?
(c) NaCN
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