7. Substitution Reactions
Substitution Comparison
43PRACTICE PROBLEM
A stereospecific reaction of 2-(tosyloxy)cyclopentyl propionate and propionate produces a product dependent on the substrate's stereoisomer. The substrate has four stereoisomers — two are cis and the other are trans—due to two asymmetric centers. Explain the observations made below.
When the reactants are both cis, it will form an optically active trans product, but each substrate would form different trans product.
![](https://lightcat-files.s3.amazonaws.com/problem_images/44b5f3a772ee2c24-1676986970777.jpg)
A stereospecific reaction of 2-(tosyloxy)cyclopentyl propionate and propionate produces a product dependent on the substrate's stereoisomer. The substrate has four stereoisomers — two are cis and the other are trans—due to two asymmetric centers. Explain the observations made below.
When the reactants are both cis, it will form an optically active trans product, but each substrate would form different trans product.