Textbook Question
Provide an arrow-pushing mechanism that rationalizes the outcome of the reaction shown.
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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 32
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 32Chapter 12, Problem 32
When SOCl2 is used in place of HCl, only one product results. Why are these conditions better?
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Identify the starting material and the reagent: The starting material is an alcohol, and the reagent is thionyl chloride (SOCl2) in the presence of a base (Et3N).
Understand the mechanism: SOCl2 converts alcohols to alkyl chlorides through a mechanism that involves the formation of an intermediate chlorosulfite ester, which then undergoes a nucleophilic substitution reaction.
Compare with HCl: When HCl is used, the reaction typically proceeds through an SN1 mechanism, which can lead to carbocation rearrangements and result in multiple products.
Explain the advantage of SOCl2: The use of SOCl2 avoids carbocation formation and rearrangement, leading to a single product through an SN2 mechanism, which is stereospecific and retains the configuration of the starting material.
Conclude why SOCl2 is better: SOCl2 provides a more controlled and predictable reaction pathway, resulting in a single, desired product without side reactions or rearrangements.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Thionyl Chloride (SOCl₂) Reactivity
Thionyl chloride is a reagent commonly used in organic synthesis for converting alcohols into alkyl chlorides. Its unique reactivity allows for the formation of a single product due to the mechanism involving the formation of a cyclic intermediate, which leads to a more controlled reaction pathway compared to other reagents like HCl.
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Synthesis of Acid Chlorides
Mechanism of Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. The mechanism can proceed via either an SN1 or SN2 pathway, influencing the number of products formed. SOCl₂ typically favors the SN2 mechanism, resulting in a single product due to its steric and electronic properties.
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Selectivity in Organic Reactions
Selectivity refers to the ability of a reaction to produce a specific product over others. In the case of SOCl₂, the reaction conditions and the nature of the reagent lead to high selectivity, minimizing side reactions and by-products. This contrasts with HCl, which can lead to multiple products due to its less selective nature in nucleophilic substitution.
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Related Practice
Textbook Question
Provide the alcohol that would be used to make the bromoalkanes shown using PBr₃.
(a)
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Textbook Question
Using an excess of HCl in the following reaction resulted in a product that was not simply the substitution of chlorine for the hydroxyl group. Predict the identity of the product obtained.
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Textbook Question
Predict the product of the following reactions.
(b)
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Textbook Question
Identify the reagent that should be used to obtain each stereochemical outcome shown.
(b)
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Textbook Question
Identify the reagent that should be used to obtain each stereochemical outcome shown.
(a)
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