Domanda del libro di testo
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ii) PBr₃ If no reaction occurs, write 'no reaction.'
(c)
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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 106f(iii,iv)
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 106f(iii,iv)Capitolo 12, Problema 106f(iii,iv)
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'
(f) 
Guida verificata passo dopo passo1
Identify the functional group in the given molecule. The structure shows a tertiary alcohol group attached to a benzene ring.
Consider the reaction conditions (iii) SOCl₂, NEt₃. This is a common method for converting alcohols to alkyl chlorides via the formation of a chlorosulfite intermediate.
In the presence of SOCl₂ and NEt₃, the hydroxyl group (OH) of the tertiary alcohol will be replaced by a chlorine atom, resulting in the formation of a tertiary alkyl chloride.
Now consider the reaction conditions (iv) 1. TsCl, Et₃N 2. NaCN. The first step involves converting the alcohol to a tosylate, which is a good leaving group, using TsCl and Et₃N.
In the second step, the tosylate reacts with NaCN, leading to a nucleophilic substitution where the tosylate group is replaced by a cyano group (CN), forming a nitrile.
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Thionyl Chloride (SOCl₂) Reactivity
Thionyl chloride is a reagent commonly used for converting alcohols into alkyl chlorides. It reacts with alcohols to form the corresponding alkyl chloride and byproducts of sulfur dioxide and hydrochloric acid. Understanding this reaction mechanism is crucial for predicting the products when alcohols are treated with SOCl₂ in the presence of a base like NEt₃, which helps to neutralize the generated HCl.
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01:36
Synthesis of Acid Chlorides
TsCl and Base Reaction
TsCl, or tosyl chloride, is used to convert alcohols into tosylates, which are better leaving groups for subsequent nucleophilic substitutions. When combined with a base like Et₃N, the tosylate can then react with nucleophiles such as NaCN in a second step. This two-step process is essential for understanding how to predict the final products of the reaction sequence involving TsCl and NaCN.
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02:43Recognizing Acid-Base Reactions.
Nucleophilic Substitution Mechanisms
Nucleophilic substitution reactions, such as SN1 and SN2, are fundamental in organic chemistry for understanding how nucleophiles attack electrophiles. The choice of mechanism depends on factors like substrate structure and the nature of the nucleophile. Recognizing whether a reaction will proceed via SN1 or SN2 is vital for predicting the outcome of reactions involving alkyl halides and nucleophiles like NaCN.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
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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.'
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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.'
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Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O If no reaction occurs, write 'no reaction.'
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Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'
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