Textbook Question
Predict the products you would get when the following alkenes react under the following conditions: (i) H2SO4, H2O and (ii) 1. Hg(OAc)2, H2O , 2. NaBH4
(c)
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Ch. 8 - Alkenes I: Properties and Electrophilic Additions
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. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 50a(i)
Mullins 1st EditionCh. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 50a(i)Chapter 7, Problem 50a(i)
Predict the products you would get when the following alkenes react under the following conditions: (i) H2SO4 , H2O
(a) 
Verified step by step guidance1
Identify the type of reaction: The reaction involves an alkene reacting with H₂SO₄ (sulfuric acid) and H₂O (water). This is an acid-catalyzed hydration reaction, which adds a water molecule (H and OH) across the double bond of the alkene.
Determine the regioselectivity: The reaction follows Markovnikov's rule, meaning the hydrogen (H) from water will add to the carbon of the double bond that has more hydrogens already attached, and the hydroxyl group (OH) will add to the carbon with fewer hydrogens.
Protonation of the alkene: The π-electrons of the alkene attack the proton (H⁺) from H₂SO₄, forming a carbocation intermediate. Ensure to consider the stability of the carbocation; if a more stable carbocation can form via rearrangement (e.g., hydride or alkyl shift), it will occur.
Nucleophilic attack: The water molecule (H₂O) acts as a nucleophile and attacks the carbocation, forming an oxonium ion (R-OH₂⁺).
Deprotonation: The oxonium ion loses a proton (H⁺) to regenerate the acid catalyst (H₂SO₄), resulting in the final product, which is an alcohol (R-OH) with the hydroxyl group added according to Markovnikov's rule.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Addition
Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes. In the presence of strong acids like H₂SO₄, the double bond of the alkene acts as a nucleophile, attacking the electrophilic hydrogen, leading to the formation of a carbocation intermediate. This process is crucial for predicting the products of alkene reactions.
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1,2 vs 1,4 Addition
Carbocation Stability
Carbocation stability is a key concept in organic reactions involving alkenes. Carbocations are positively charged carbon species that can form during electrophilic addition reactions. Their stability is influenced by factors such as the degree of substitution (primary, secondary, tertiary) and resonance. Understanding which carbocation is formed helps predict the final product of the reaction.
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Hydration Reaction
The hydration reaction refers to the addition of water (H₂O) to an alkene, resulting in the formation of an alcohol. When alkenes react with H₂SO₄ followed by water, the process involves the initial formation of a carbocation, which is then attacked by water. This reaction is essential for converting alkenes into alcohols and is a common transformation in organic synthesis.
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Related Practice
Textbook Question
Predict the products you would get when the following alkenes react under the following conditions: (i) H2SO4, H2O and (ii) 1. Hg(OAc)2, H2O , 2. NaBH4
(d)
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Textbook Question
Provide a mechanism for the following reactions occurring with rearrangement.
(b)
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Textbook Question
Predict the products you would get when the following alkenes react under the following conditions: (ii) 1. Hg(OAc)2 , H2O , 2. NaBH4
(a)
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Textbook Question
Our wayward chemist from Assessment 8.23 suggested the following stepwise mechanism for a hydride shift. Show this mechanism on a reaction coordinate diagram to illustrate why the concerted mechanism is more likely. Justify the picture you have drawn.
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Textbook Question
The hydration of three C5H10 alkene isomers can give 2-methylbutan-2-ol. Draw them.
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