ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
12th Edition
ISBN: 9781119766919
Author: Solomons
Publisher: WILEY
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Chapter 23, Problem 3PP
Interpretation Introduction

Interpretation:

The products obtained when the given terpenes are subjected to ozonolysis and then treated with dimethyl sulphide are to be determined.

Concept Introduction:

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The essential oils are odoriferous chemicals that are extracted from plants by heating or distillation. These essential oils have important chemical composition of hydrocarbons called terpenes and oxygen-containing compounds called terpenoids. The monoterpene unit is made up of two or more 5-Carbon atoms.

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The ozone is a powerful oxidant and the terpenoid alkenes (or any other alkenes) undergo cleavage with ozone to produce a range of byproducts. The reaction cleaves the alkene into two carbonyl products with the formation of an ozonide as an intermediate. This ozonide undergoes reduction with dimethyl sulphide ( (CH3)2S ) to yield aldehyde(s).

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The ozonolysis of myrcene produces 1 mol of monoterpene, 2 mols of formaldehyde, and 1 mol of acetone.

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The limonene undergoes ozonolysis and reduction process to yield the products, 1 mol of formaldehyde and 1 mol of monoterpene.

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The αFarnesene undergoes ozonolysis, and reduction reaction by dimethyl sulphide, to give the products, 1 mol of a primary carbonyl (acetone), 1 mol of a secondary carbonyl (aldehyde-keto group), 1 mol of an aldol (hydroxy butanal), 1 mol of glyoxal (ethanediol), and 1 mol of formaldehyde

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The geraniol undergoes ozonolysis followed by reduction reaction by dimethyl sulphide to produce 1 mol of a primary carbonyl (acetone), 1 mol of a secondary carbonyl (aldehyde-keto group), and 1 mol of glyoxal (ethanediol).

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The products formed by the reaction of ozone and dimethyl sulphide with squalene are 2 mols of acetone, 1 mol of hydroxy-aldehyde, and 4 mols of a ketal.

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