Question

What alkene with the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{12}\), when treated with ozone and then dimethyl sulfide, gives the following product(s)? (a) CCC=O (b) CCC(=O)[C+]C(C)=O (c) CC(C)=O (only product) (equal moles of each) (only product)

Short answer

Answer: The alkene that gives the corresponding products when treated with ozone and dimethyl sulfide is (smiles)C=CCCC=C(/smiles).

Step-by-step solution

Determining the alkene for product (a)

The given product (a) is acetaldehyde & has structure: (smiles)CC=O(/smiles) To determine the corresponding alkene that generated this product, we should perform reverse ozonolysis on this compound. The reverse process would involve the splitting of the carbonyl double bond and connecting both carbons with a double bond and two hydrogen atoms. The resulting alkene is: (smiles)C=CCC(/smiles)

Determining the alkene for product (b)

The given product (b) is a combination of two molecules, which are: (smiles)CC(=O)C(/smiles) and (smiles)C(=O)C=C(/smiles) Performing reverse ozonolysis on both molecules, we get the alkene: (smiles)C=CCCC=C(/smiles)

Determining the alkene for product (c)

The given product (c) is acetone & has structure: (smiles)CC(C)=O(/smiles) Reverse ozonolysis of this compound gives us the alkene: (smiles)CC=CC(/smiles)

Comparing alkenes and selecting the correct structure

Now, we need to find the alkene with the molecular formula C6H12. Comparing the alkenes in step 1, 2, and 3, only the alkene from step 2 has a molecular formula of C6H12: (smiles)C=CCCC=C(/smiles) Therefore, the alkene that gives the corresponding products when treated with ozone and dimethyl sulfide is the one found in step 2.