Domanda del libro di testo
Triphenylphosphine and iodine can be used to convert alcohols to iodoalkanes. Suggest a mechanism for this reaction. [Triphenylphosphine first acts as a nucleophile in this reaction.]
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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
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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 106o(i-xii)
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 106o(i-xii)Capitolo 12, Problema 106o(i-xii)
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.'
(o) 
Guida verificata passo dopo passo1
Identify the functional group in the given molecule. The structure shows a secondary alcohol attached to a benzene ring.
Consider the reaction with SOCl₂. This reagent typically converts alcohols into alkyl chlorides via an SN2 mechanism, which may lead to inversion of configuration.
For the reaction with PBr₃, expect a similar transformation as with SOCl₂, converting the alcohol into an alkyl bromide, again with potential inversion of configuration.
When SOCl₂ is used with NEt₃, the reaction proceeds similarly to SOCl₂ alone, but NEt₃ acts as a base to neutralize the HCl byproduct, facilitating the formation of the alkyl chloride.
For the reaction sequence with TsCl and Et₃N followed by NaCN, the alcohol is first converted to a tosylate, which is a good leaving group, and then undergoes nucleophilic substitution with NaCN to form a nitrile.
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Reagents and Their Functions
Understanding the specific reagents mentioned in the question, such as SOCl₂, PBr₃, and TsCl, is crucial. Each reagent has distinct roles in organic reactions, such as converting alcohols to alkyl halides or facilitating nucleophilic substitutions. Familiarity with these reagents helps predict the products formed during the reactions.
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Identifying Functional Groups
Mechanisms of Organic Reactions
Organic reactions often follow specific mechanisms, such as SN1, SN2, E1, or E2 pathways. Recognizing the mechanism allows for predicting the outcome of reactions based on the structure of the reactants and the conditions provided. This understanding is essential for determining whether a reaction will proceed and what products will be formed.
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02:17Identifying organic molecules
Functional Group Transformations
Functional groups are specific groups of atoms within molecules that determine their chemical reactivity. The question involves various transformations, such as oxidation and substitution, which change the functional groups present in the reactants. A solid grasp of how different functional groups react under various conditions is vital for accurately predicting the products.
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02:36Identifying Functional Groups
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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.'
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Another method for converting alcohols to chloroalkanes makes use of chlorotrimethylsilane (TMSCl) and DMSO. Suggest a mechanism for this reaction to form (a) a 1° chloroalkane and (b) a 3° chloroalkane. [The reaction begins by the reaction of DMSO and TMSCl and is analogous to the Swern oxidation.]
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