Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
Question
Book Icon
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:

>

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.

>

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).

>

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

>

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

>

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

>

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).

>

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.

Blurred answer
Students have asked these similar questions
Write the structure of the principal organic product obtained on nitration of each of the following: (a) p-Methylbenzoic acid (d) p-Methoxyacetophenone (b) m-Dichlorobenzene (e) p-Methylanisole (c) m-Dinitrobenzene (f ) 2,6-Dibromoanisole
Each of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)
The following questions pertain to the esters shown and behavior under conditions of the Claisen condensation.(a) Two of these esters are converted to β-keto esters in good yield on treatment with sodium ethoxide and subsequent acidification of the reaction mixture. Which two are these? Write the structure of the Claisen condensation product of each one. (b) One ester is capable of being converted to a β-keto ester on treatment with sodium ethoxide, but the amount of β-keto ester that can be isolated after acidification of the reaction mixture is quite small. Which ester is this? (c) One ester is incapable of reaction under conditions of the Claisen condensation. Which one? Why?
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning