Explanation The hydration of alkene is an addition reaction of water in the presence of acid. Hence, this addition takes place as per the Markovnikov’s rule, which states that hydrogen atoms are added to carbons associated by a double bond carrying the greater number of hydrogen atoms. This forms carbonation and then a nucleophilic attack to form alcohol. Only ethylene is a molecule which forms a primary carbocation, while in any other alkene, either 2 0 and 3 0 carbocations are formed, giving 2 0 and 3 0 alcohols. Only ethylene gives 1 0 alcohol.

Introduction to General, Organic and Biochemistry

12th Edition

ISBN: 9780357391594

Author: Frederick A. Bettelheim; William H. Brown; Mary K. Campbell

Publisher: Cengage Learning US

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Question

Chapter 12, Problem 39P

Interpretation Introduction

Interpretation:

Why the acid-catalyzed hydration of alkenes cannot be used to prepare primary alcohol? And provide the reasoning as well.

Concept introduction:

During the hydration of alkene the unsaturated alkene converted into saturated alkane with the addition of H+ and OH- ions in the presence of H₂ SO₄. This reaction is carried out in the presence of acid therefore it is called acid catalyzed hydration of alkene.

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Chapter 12 Solutions

Introduction to General, Organic and Biochemistry

Ch. 12.3 - Prob. 12.1QC Ch. 12.3 - Prob. 12.2QC Ch. 12.3 - Problem 12-3 Write the IUPAC name for each...Ch. 12.3 - Problem 12-4 Draw structural formulas for the...Ch. 12.3 - Problem 12-5 How many stereoisomers are possible...Ch. 12.5 - Prob. 12.6QC Ch. 12.5 - Problem 12-7 Propose a two-step mechanism for the...Ch. 12.5 - Prob. 12.8QC Ch. 12.5 - Problem 12-9 Propose a three-step reaction...Ch. 12.5 - Prob. 12.10QC

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