Domanda del libro di testo
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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TOC.tableOfContents
- 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 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: 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 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: 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: 9780137566471Non è quello che usi tu?Cambia libro di testo
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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 106a(i,ii)
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 106a(i,ii)Capitolo 12, Problema 106a(i,ii)
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) 
Guida verificata passo dopo passo1
Identify the functional group in the given molecule. The structure shown is benzyl alcohol, which contains a hydroxyl group (-OH) attached to a benzyl group.
Consider the reaction with thionyl chloride (SOCl₂). Thionyl chloride is commonly used to convert alcohols into alkyl chlorides. The hydroxyl group will be replaced by a chlorine atom.
Write the mechanism for the reaction with SOCl₂. The reaction typically involves the formation of an intermediate chlorosulfite ester, followed by the release of sulfur dioxide (SO₂) and hydrogen chloride (HCl), resulting in the formation of benzyl chloride.
Consider the reaction with phosphorus tribromide (PBr₃). PBr₃ is used to convert alcohols into alkyl bromides. The hydroxyl group will be replaced by a bromine atom.
Write the mechanism for the reaction with PBr₃. The reaction involves the formation of an intermediate dibromophosphite ester, followed by the release of phosphorous acid (H₃PO₃), resulting in the formation of benzyl bromide.
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Thionyl Chloride (SOCl₂) Reactivity
Thionyl chloride is a reagent commonly used for converting alcohols into alkyl chlorides. The reaction proceeds through the formation of an intermediate that facilitates the substitution of the hydroxyl group with a chlorine atom. Understanding the mechanism of this reaction, including the role of the leaving group and the formation of byproducts like sulfur dioxide and hydrochloric acid, is essential for predicting the products.
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01:36
Synthesis of Acid Chlorides
Phosphorus Tribromide (PBr₃) Reactivity
Phosphorus tribromide is another reagent used to convert alcohols into alkyl bromides. The mechanism involves the formation of an intermediate that allows for the substitution of the hydroxyl group with a bromine atom. Recognizing the conditions under which PBr₃ operates, including its preference for primary and secondary alcohols, is crucial for determining the expected products of the reaction.
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01:17Reactivity of Molecules
Substitution Reactions
Substitution reactions are fundamental organic reactions where one functional group is replaced by another. In the context of alcohols reacting with SOCl₂ and PBr₃, the hydroxyl group is substituted by a halogen. Understanding the types of substitution mechanisms, such as SN1 and SN2, helps in predicting the outcome of reactions based on the structure of the starting materials and the conditions provided.
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01:34Recognizing Substitution Reactions.
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