Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 8, Problem 48P

(a)

Interpretation Introduction

Interpretation: The major product needs to be determined for the following reaction:

  Organic Chemistry: Structure and Function, Chapter 8, Problem 48P , additional homework tip  1

Concept Introduction: The oxidation of secondary alcohol results in the formation of ketone. The general reaction is represented as follows:

  Organic Chemistry: Structure and Function, Chapter 8, Problem 48P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation: The major product needs to be determined for the following reaction:

  Organic Chemistry: Structure and Function, Chapter 8, Problem 48P , additional homework tip  3

Concept Introduction: The PCC is abbreviation for pyridinium chlorochromate. It shows partial oxidation of alcohol to aldehyde.

(c)

Interpretation Introduction

Interpretation: The major product needs to be determined for the following reaction:

  Organic Chemistry: Structure and Function, Chapter 8, Problem 48P , additional homework tip  4

Concept Introduction: The oxidation of secondary alcohol results in the formation of ketone. The general reaction is represented as follows:

  Organic Chemistry: Structure and Function, Chapter 8, Problem 48P , additional homework tip  5

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H3C CH3 H3C NA C→XT Br Br₂ CH₂Cl₂ H3C Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂. CH3 Br In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br CH3 H3C CH3
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Write the structure of the major products in the following reactions and name them.
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