Textbook Question
The reaction of alkoxides with haloalkanes is not a viable way to form ethers. (a) Why? (b) Why can thioethers be formed by an analogous 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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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 106a(vi)
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 106a(vi)Chapter 12, Problem 106a(vi)
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vi) H₂SO₄. If no reaction occurs, write 'no reaction.'
(a) 
Verified step by step guidance1
Identify the functional group in the given molecule. The structure shows a benzene ring with a primary alcohol group attached, known as benzyl alcohol.
Consider the reaction conditions: H₂SO₄ is a strong acid and can act as a dehydrating agent.
Recognize that under acidic conditions, primary alcohols can undergo dehydration to form alkenes. In this case, benzyl alcohol can lose a water molecule to form a double bond.
Propose the mechanism: The hydroxyl group (OH) will be protonated by H₂SO₄, making it a better leaving group. This will lead to the formation of a carbocation.
Predict the product: The carbocation formed can lose a proton to form a double bond, resulting in the formation of styrene (phenylethene) as the major product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Reactions
In organic chemistry, acid-base reactions involve the transfer of protons (H⁺) between molecules. Strong acids, like sulfuric acid (H₂SO₄), can donate protons to bases, facilitating various reactions such as dehydration or protonation. Understanding the role of acids and bases is crucial for predicting the outcome of reactions involving functional groups.
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The Lewis definition of acids and bases.
Electrophilic Addition
Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, leading to the formation of a more saturated product. In the presence of H₂SO₄, alkenes and alkynes can undergo electrophilic addition, resulting in the formation of carbocations and subsequent products. Recognizing the nature of the reactants helps in predicting the products formed.
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Reaction Conditions
The conditions under which a reaction occurs significantly influence the products formed. In this case, the presence of concentrated sulfuric acid can lead to dehydration reactions, where water is removed from alcohols or alkenes, forming alkenes or ethers. Understanding how temperature, concentration, and solvent affect reaction pathways is essential for accurate predictions.
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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.'
(a)
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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: (ix) PCC; (x) H₂CrO₄ , H₂O. If no reaction occurs, write 'no reaction.'
(a)
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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: (iv) 1. TsCl, Et₃N 2. NaCN ; (v) 1. TsCl, Et₃N 2. NaOt-Bu . If no reaction occurs, write 'no reaction.'
(a)
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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. If no reaction occurs, write 'no reaction.'
(a)
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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: (iii) SOCl2 , NEt3. If no reaction occurs, write 'no reaction.'
(a)
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