Question

draw the structure of an eight‑carbon alkene that would yield the following compound (and no others) after treatment with ozone followed by dimethyl sulfide.

Answer 1

The eight-carbon alkene yielding the specified compound post-ozonolysis and treatment with dimethyl sulfide is 4,4-dimethyloct-2-ene, due to its symmetrical structure leading to a single product.

Step-by-step explanation:

The structure of an eight-carbon alkene that would yield the desired compound with no others after treatment with ozone followed by dimethyl sulfide likely involves a symmetrical alkene to avoid forming multiple ozonolysis products. In this case, the alkene should be 4,4-dimethyloct-2-ene. Upon ozonolysis, a symmetrical alkene like this would cleave to form two identical carbonyl compounds, which, after reduction with dimethyl sulfide, will result in a single product. This controlled reaction is due to the symmetrical nature of the alkene that splits into two equal fragments.

Answer 2

The question involves the structure of an eight-carbon alkene that yields a single product after ozonolysis, suggesting a symmetrical alkene like 4-octene being cleaved to form two molecules of butanal.

Step-by-step explanation:

The student's question pertains to the process of ozonolysis, which is a chemical reaction where an alkene is cleaved with ozone to form carbonyl compounds. After the treatment with dimethyl sulfide, one typically ends up with either aldehydes or ketones, or both, depending on the position of the double bond in the original alkene. For an eight-carbon alkene to produce only one specific compound upon reaction with ozone followed by treatment with dimethyl sulfide, it implies that the alkene must contain a symmetrical double bond, such that both halves of the molecule are identical.

An example of such an alkene would be 4-octene, where the double bond is positioned between the fourth and fifth carbon atoms, making the halves of the molecule mirror images of each other. After ozonolysis and reduction with dimethyl sulfide, 4-octene would yield two molecules of an identical aldehyde, specifically butanal, as the only product.