Organic Chemistry: Principles And Mechanisms (second Edition)
Organic Chemistry: Principles And Mechanisms (second Edition)
2nd Edition
ISBN: 9780393630749
Author: KARTY, Joel
Publisher: W. W. Norton & Company
Question
Book Icon
Chapter 12, Problem 12.43P
Interpretation Introduction

(a)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3< 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Interpretation Introduction

(b)

Interpretation:

How to prepare the given compound from an alkene is to be explained.

Concept introduction:

The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the C=C bond in an acidic condition. The electrophilic addition reaction of an alkene occurs through formation of a more stable carbocation. The reaction proceeds with proton transfer reaction to form a stable carbocation, followed by the action of water as a nucleophile, forming the corresponding alcohol. The order of stability of carbocation is CH3< 1o < 2o < 3o. The carbocation can be rearranged by 1, 2- hydride or 1, 2- methyl shift to form a more stable carbocation.

The oxymercuration-reduction is also the reaction of addition of water through the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The mechanism follows the Markovnikov rule and adds OH to more substituted double bonded carbon. The reaction proceeds through formation of a Mercurinium ion intermediate, and there is no formation of a carbocation. Thus, the rearrangement is not possible in oxymercuration-reduction.

Blurred answer
Students have asked these similar questions
Identify the missing organic reactants in the following reaction: X + Y H+ two steps Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H2O) are not shown. In the drawing area below, draw the skeletal ("line") structures of the missing organic reactants X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. Х :
Draw the mechanism of friedel-crafts acylation using acetyl chloride of m-Xylene
I need help naming these in IUPAC

Chapter 12 Solutions

Organic Chemistry: Principles And Mechanisms (second Edition)

Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning