Question

Compounds X and Y are stereoisomers having the formula C6H12. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form hexane, and they each react with HBr to give a single bromoalkane product. Draw structural formulas for both X and Y.

Answer 1

(E)-3-hexene and (Z)-3-hexene

Step-by-step explanation:

From the first clue we know that the posible structures have linear structures, therefore we will have as options 1-hexene, 2-hexene and 3-hexene.

Using the second clue, we only have 1 product for the HBr addition. In the 1-hexene we only have 1 product for the HBr addition, but we need two molecules to answer the question, so, this molecule can be discarded. For 2-hexene we will have 2 products in the HBr addition, so, this molecule can be discarded also (figure 2). Finally, for the last option 3-hexene we will have 2 options the E isomer (cis) and the Z isomer (trans) both molecules will have the same product in the HBr addition (figure 1).