Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 28, Problem 38P

(a)

Interpretation Introduction

Interpretation:

A mechanism should be proposed for the given reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or brocken in a cyclic transition state”.  There is a single transition state from start to finish, in contrast to a stepwise reaction.

In an electrocyclic reaction “one new sigma- bond is formed or brocken.”

Organic Chemistry (8th Edition), Chapter 28, Problem 38P , additional homework tip  1

Diels-alder reaction is a cycloaddition reaction which is occurs between a conjugated diene and substituted alkene to form cyclohexene ring system.  This concerted reaction can be accelerated by heating or using some catalysts.

Mechanism gives the step wise processes occurs in a particular reaction.

(b)

Interpretation Introduction

Interpretation:

The product should be determined for the given reaction if trans-2-butene were used instead of ethene.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or brocken in a cyclic transition state”.  There is a single transition state from start to finish, in contrast to a stepwise reaction.

In an electrocyclic reaction “one new sigma- bond is formed or brocken.”

Organic Chemistry (8th Edition), Chapter 28, Problem 38P , additional homework tip  2

Diels-alder reaction is a cycloaddition reaction which is occurs between a conjugated diene and substituted alkene to form cyclohexene ring system.  This concerted reaction can be accelerated by heating or using some catalysts.

Mechanism gives the step wise processes occurs in a particular reaction.

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Exp3: Diels-Alder reaction   Why does cyclopentadiene regularly form a dimer? How to break the dimer into monomers? Does the diene in this reaction act as the nucleophile or the electrophile? Is the maleic anhydride a nucleophile or an electrophile in this reaction? Explain your reasoning.
1. In a Birch reaction, an aromatic compound can be treated with Na/CH3OH, it can also be treated with Li/NH3 and have the same product form. One of the intermediates in the Birch reaction is a radical anion. In the example below, anisole could possibly form a radical anion A or B, then will go into C and D. Li/NH3 A B C D A. With the knowledge you have gained from what we have discussed, which anion A or B is more stable? What is your reasoning? B. Is a Birch reaction and oxidation or reduction? Why?
Provide explanation.
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