Question

Compound A is an alkene that was treated with ozone to yield only (CH3CH2CH2)2C=O. Draw the major product that is expected when compound A is treated with a peroxy acid (RCO3H) followed by aqueous acid (H3O+).

Answer 1

Answer:

2,2,3,3-tetrapropyloxirane

Explanation:

In this case, we have to know first the alkene that will react with the peroxyacid. So:

What do we know about the unknown alkene?

We know the product of the ozonolysis reaction (see figure 1). This reaction is an oxidative rupture reaction. Therefore, the double bond will be broken and we have to replace the carbons on each side of the double bond by oxygens. If $(CH_3CH_2CH_2)_2C=O$ is the only product we will have a symmetric molecule in this case 4,5-dipropyloct-4-ene.

What is the product with the peroxyacid?

This compound in the presence of alkenes will produce peroxides. Therefore we have to put a peroxide group in the carbons where the double bond was placed. So, we will have as product 2,2,3,3-tetrapropyloxirane. (see figure 2)