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)
1
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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 106c(ii)
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 106c(ii)Chapter 12, Problem 106c(ii)
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) 
Verified step by step guidance1
Identify the functional groups in the given molecule. The structure shows a cyclohexane ring with two hydroxyl groups (OH) attached, indicating it is a diol.
Understand the role of PBr₃ in organic reactions. Phosphorus tribromide (PBr₃) is commonly used to convert alcohols into alkyl bromides by replacing the hydroxyl group with a bromine atom.
Determine which hydroxyl group will react with PBr₃. PBr₃ typically reacts with primary and secondary alcohols. In this molecule, both hydroxyl groups are secondary, so both can potentially react.
Predict the reaction mechanism. The reaction with PBr₃ involves the formation of a phosphite ester intermediate, followed by the substitution of the hydroxyl group with a bromine atom, resulting in the formation of an alkyl bromide.
Consider the stereochemistry of the reaction. The reaction with PBr₃ usually proceeds with inversion of configuration at the carbon atom bearing the hydroxyl group, due to the SN2 mechanism involved.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
PBr₃ Reaction with Alcohols
Phosphorus tribromide (PBr₃) is commonly used to convert alcohols into alkyl bromides. The reaction involves the substitution of the hydroxyl group (OH) with a bromine atom (Br), resulting in the formation of an alkyl bromide. This reaction is typically used for primary and secondary alcohols, as it proceeds via an SN2 mechanism, which is less favorable for tertiary alcohols due to steric hindrance.
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01:44
Forming alcohols through SN2 reactions.
SN2 Mechanism
The SN2 mechanism is a bimolecular nucleophilic substitution reaction where the nucleophile attacks the electrophilic carbon from the opposite side of the leaving group, resulting in an inversion of configuration. This mechanism is favored in primary and secondary alcohols due to less steric hindrance, allowing the nucleophile to effectively approach the carbon atom. In the context of PBr₃ reactions, the bromide ion acts as the nucleophile, replacing the hydroxyl group.
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08:33Drawing the SN2 Mechanism
Vicinal Diols
Vicinal diols are compounds with two hydroxyl groups attached to adjacent carbon atoms. In the given structure, the presence of vicinal diols can influence the reaction pathway, as they may undergo rearrangement or elimination under certain conditions. However, with PBr₃, each hydroxyl group can independently react to form the corresponding alkyl bromide, assuming no rearrangement occurs.
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03:50General properties of syn vicinal dihydroxylation.
Related Practice
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.'
(c)
5
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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)
1
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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.'
(c)
2
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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)
Textbook Question
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)
2
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