ORGANIC CHEMISTRY SAPLING ACCESS + ETEX
ORGANIC CHEMISTRY SAPLING ACCESS + ETEX
6th Edition
ISBN: 9781319306977
Author: LOUDON
Publisher: INTER MAC
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Chapter 28, Problem 28.54AP
Interpretation Introduction

(a)

Interpretation:

The type of pericyclic reaction required to form benzene from Dewar benzene is to be stated.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 28, Problem 28.54AP

Concept introduction:

The isomer of benzene having bicyclic ring with the molecular formula of C6H6 is termed as Dewar benzene or bicyclo [2, 2, 0] hexa-2, 5-diene. This structure is included in the list of possible structure of benzene and named after James Dewar. However, this bicyclic ring structure is not accepted as the true structure of benzene and Dewar supported the Kekule structure of benzene.

Interpretation Introduction

(b)

Interpretation:

Dewar benzene, although a very unstable molecule, is not readily transformed to benzene is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time. Notably, the pericyclic reactions are classified as electrocyclic, cycloaddition and sigmatropic reactions based on the activation of reaction, the number of electrons involved and the stereochemistry outcome of the reactions.

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A. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?
Where are the chiral centers in this molecule? Also is this compound meso yes or no?
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