🤓 Based on our data, we think this question is relevant for Professor Cerkez's class at TEMPLE.

Solution: An unknown alkene gives propanal as the only product upon ozonolysis (reductive workup). When the unknown is treated with bromine in carbon tetrachloride, an optically inactive dibromide is formed, which cannot be resolved into enantiomers. Which of these alkenes is consistent with this data?

Problem

An unknown alkene gives propanal as the only product upon ozonolysis (reductive workup). When the unknown is treated with bromine in carbon tetrachloride, an optically inactive dibromide is formed, which cannot be resolved into enantiomers. Which of these alkenes is consistent with this data?