Showing posts with label Ozonolysis. Show all posts
Showing posts with label Ozonolysis. Show all posts

Wednesday, November 27, 2013

Find the final product

Question: What will be the final product P of the following reaction?




Solution: To find out the final product let us treat the given reactant with the reagent step by step:

First the given reactant is treated with H3O+.


[H30]+ is a hydronium cation, also known as hydroxonium. It's an acid according to Bronstend-Lowry theory, about bases and acids, because it can give of a [H]+ :

[H30] <--> H2O + H+
So when given reactant reacts with H3O+, it gives:



On heating the obtained product losses CO2



Now the obtained alkene is react with O3 and H2O2.

As a reagent, ozone is used to cleave alkenes. When alkenes are treated with ozone and H2O2, they are subjected to “Oxidative workup”, this breaks the carbon-carbon double bond to form carboxylic acid. 



Now this is final product P. 

Wednesday, April 10, 2013

Problem on ozonolysis


Question: How many optically active products are obtained when the given compound is treated with ozone followed by Zn in acetic acid?




Solution: At first look the question seems very complex. But there is nothing like that. This question is a combination of two different topics, one is ozonolysis and another is optical active compound. We can solve this problem by applying simple basics of the topics. So let us start.

The given compound is an alkene (due to presence of double bonds). When ozone (O3) reacts with alkene, it breaks the double bond and form an intermediate compound called ozonide. This ozonide on treatment with reducing agent gives aldehyde or ketone while on treatment with oxidizing agent it gives carboxylic acid.


 


In the given question, Zn in acetic acid is used during ozonolysis which is a reducing agent. Thus the given compound on complete ozonolysis gives:


 


Now the next step of question: To check whether the obtained products are optically active or not, for this let us check their chirality.

Compounds that are optically active contain molecule that are chiral.  A chiral molecule is not superimposable on its mirror image.





Molecule 1 is not superimposable on its mirror image and therefore is chiral and optically active.



Molecule 3 is superimposible on its mirror image and therefore is achiral and optically inactive.


Now let us check products obtained after ozonolysis.

Thus, all the obtained products during ozonolysis are achiral. Means there is no optically active compound is formed.