ORGANIC CHEM +SG +SAPLING >IP<
ORGANIC CHEM +SG +SAPLING >IP<
6th Edition
ISBN: 9781319171179
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 28, Problem 28.34AP
Interpretation Introduction

(a)

Interpretation:

When compound A is irradiated with ultraviolet light for 115 hours in pentane, an isomeric compound B is obtained that decolorizes bromine in CH2Cl2 and reacts with ozone to give, after the usual workup, a compound C.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 28, Problem 28.34AP

The structure of B and the stereochemistry of both B and C is to be given.

Concept introduction:

Cycloaddition reaction can be referred as a reaction of two different π-electron systems to form a ring product. Notably, in this reaction two new sigma bonds are formed in product with the disappearance of two fewer π-bonds. In other words, cyclo addition reaction can be best described as the reaction of number of electrons involved. In [4+2] cycloaddition one component is having four electrons and other component is having two electrons.

Interpretation Introduction

(b)

Interpretation:

On heating to 90 °C, compound D, a stereoisomer of B, is converted into A, but compound B is virtually inert under the same conditions. The compound D is to be identified with reasons.

Concept introduction:

Cycloaddition reaction can be referred as a reaction of two different π-electron systems to form a ring product. Notably, in this reaction two new sigma bonds are formed in product with the disappearance of two fewer π-bonds. In other words, cyclo addition reaction can be best described as the reaction of number of electrons involved. In [4+2] cycloaddition one component is having four electrons and other component is having two electrons.

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