Textbook Question
Show an arrow-pushing mechanism that rationalizes formation of the two products. Which C―O bond will break first? Why?
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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 76
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 76Chapter 12, Problem 76
Predict the alcohol and haloalkane that will form upon reaction of the ether shown with one equivalent of HBr. [Hint: Think carefully about which side will become the halide.]
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Identify the structure of the ether. Ethers have the general formula R-O-R', where R and R' are alkyl groups. Determine the specific alkyl groups present in the given ether.
Understand the mechanism of ether cleavage by HBr. Ethers react with HBr through a nucleophilic substitution mechanism, where the ether oxygen is protonated, making it a better leaving group.
Consider the stability of the carbocations that would form if the ether were to cleave. The more stable carbocation will dictate which side of the ether will form the haloalkane.
Determine which side of the ether will form the alcohol. The side that does not form the carbocation will retain the oxygen, resulting in the formation of an alcohol.
Predict the products: Based on the stability analysis, predict the alcohol and haloalkane that will form. The more stable carbocation side will form the haloalkane, and the other side will form the alcohol.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ether Cleavage
Ether cleavage is a reaction where an ether is split into two products, typically an alcohol and a haloalkane, upon treatment with a strong acid like HBr. The reaction involves the protonation of the ether oxygen, making it susceptible to nucleophilic attack, leading to the formation of the two products.
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Cleavage of Phenyl Ethers Concept 1
Regioselectivity in Ether Cleavage
Regioselectivity in ether cleavage refers to the preference for breaking the C-O bond on one side of the ether over the other. This is influenced by factors such as steric hindrance and the stability of the resulting carbocation. Typically, the bond that leads to the more stable carbocation is cleaved, forming the haloalkane.
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Carbocation Stability
Carbocation stability is crucial in determining the outcome of reactions involving carbocations. Stability is influenced by factors such as the number of alkyl groups attached to the positively charged carbon, resonance, and hyperconjugation. More substituted carbocations are generally more stable, guiding the regioselectivity of reactions like ether cleavage.
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