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 21a
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 21aChapter 12, Problem 21a
Which of the following bases would favorably deprotonate a hydroxyl group?
(a) 
Verified step by step guidance1
Identify the hydroxyl group in the molecule. The hydroxyl group is characterized by an -OH functional group.
Understand the concept of deprotonation. Deprotonation involves the removal of a proton (H⁺) from the hydroxyl group, resulting in the formation of an alkoxide ion (RO⁻).
Consider the strength of the base. A strong base is required to deprotonate the hydroxyl group effectively. Organolithium compounds, such as the one shown in the image, are strong bases due to the presence of the negatively charged carbon atom.
Evaluate the ability of the base to deprotonate the hydroxyl group. The base shown in the image is an organolithium compound, which is known for its ability to deprotonate alcohols due to its high basicity.
Conclude that the organolithium compound depicted in the image is a suitable base for deprotonating a hydroxyl group, as it can effectively remove the proton from the -OH group, forming an alkoxide ion.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Deprotonation
Deprotonation is the process of removing a proton (H+) from a molecule, resulting in the formation of a conjugate base. In organic chemistry, this is often facilitated by a base, which is a substance that can accept protons. Understanding the strength and nature of the base is crucial, as stronger bases are more effective at deprotonating weak acids, such as hydroxyl groups.
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Hydroxyl Group
A hydroxyl group (-OH) is a functional group consisting of an oxygen atom bonded to a hydrogen atom. It is characteristic of alcohols and phenols and can act as a weak acid, meaning it can donate a proton. The ability of a base to deprotonate a hydroxyl group depends on the stability of the resulting alkoxide ion and the strength of the base used.
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Base Strength
Base strength refers to the ability of a substance to accept protons. Strong bases, such as alkoxides or hydroxides, are more effective at deprotonating hydroxyl groups compared to weak bases. The strength of a base is often determined by its position on the pKa scale, where lower pKa values indicate stronger acids and thus stronger conjugate bases.
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Related Practice
Textbook Question
When a secondary haloalkane is treated with sodium ethoxide in ethanol, we predict alkene formation over ether formation. How did we make this determination?
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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?
(b) NaOH
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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?
(c) NaCN
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