Textbook Question
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (xi) HOCl, H₂O (xii) HIO₄. If no reaction occurs, write 'no reaction.'
(a)
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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 106a(iii)
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 106a(iii)Chapter 12, Problem 106a(iii)
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl2 , NEt3. If no reaction occurs, write 'no reaction.'
(a) 
Verified step by step guidance1
Identify the functional group in the given molecule. The structure shows a benzyl alcohol, which has a hydroxyl group (-OH) attached to a benzyl group.
Understand the role of the reagents: SOCl2 (thionyl chloride) is commonly used to convert alcohols into alkyl chlorides. NEt3 (triethylamine) acts as a base to neutralize the HCl produced during the reaction.
Predict the reaction mechanism: The hydroxyl group of the benzyl alcohol will react with SOCl2, leading to the formation of a benzyl chloride. The reaction proceeds via the formation of an intermediate chlorosulfite ester, which then decomposes to form the alkyl chloride.
Consider the stereochemistry: Since the starting material is benzyl alcohol, which is not chiral, the stereochemistry is not a concern in this reaction.
Write the expected product: The product of this reaction will be benzyl chloride, where the hydroxyl group is replaced by a chlorine atom.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Thionyl Chloride (SOCl2) Reaction with Alcohols
Thionyl chloride (SOCl2) is commonly used to convert alcohols into alkyl chlorides. The reaction involves the substitution of the hydroxyl group (OH) with a chlorine atom (Cl), facilitated by the formation of a chlorosulfite intermediate. This reaction is often carried out in the presence of a base, such as triethylamine (NEt3), to neutralize the HCl byproduct and drive the reaction to completion.
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Forming alcohols through SN2 reactions.
Role of Triethylamine (NEt3)
Triethylamine (NEt3) acts as a base in reactions involving thionyl chloride and alcohols. Its primary role is to capture the hydrogen chloride (HCl) produced during the reaction, preventing the formation of acidic conditions that could lead to side reactions or decomposition of the product. By neutralizing HCl, NEt3 helps in maintaining a favorable environment for the conversion of alcohols to alkyl chlorides.
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Reactivity of Benzyl Alcohol
Benzyl alcohol, characterized by a hydroxyl group attached to a benzene ring, is a primary alcohol that readily undergoes substitution reactions. In the presence of thionyl chloride and a base, benzyl alcohol can be efficiently converted to benzyl chloride. The aromatic ring does not participate directly in the reaction, but its presence can influence the reaction conditions and the stability of intermediates.
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Related Practice
Textbook Question
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃. If no reaction occurs, write 'no reaction.'
(a)
870
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Textbook Question
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (iii) SOCl₂, NEt₃. If no reaction occurs, write 'no reaction.'
(c)
585
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Textbook Question
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vi) H₂SO₄. If no reaction occurs, write 'no reaction.'
(a)
681
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Textbook Question
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃ ; (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ (vii) HCl; (viii) HBr; (ix) PCC; (x) H₂CrO₄ , H₂O (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'
(c)
710
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Textbook Question
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vii) HCl; (viii) HBr. If no reaction occurs, write 'no reaction.'
(a)
760
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