Question

Compound A (C₆H₁₂) reacts with 1 molar equivalent of H₂ over a Pd catalyst and yields the product(s) below on oxidative cleavage with KMnO₄ in acidic solution. Propose a structure for Compound A.

A) Hexane
B) Cyclohexene
C) Methylcyclopentane
D) 3-Methylpentane

Answer 1

Compound A is most likely cyclohexene, as it reacts with one molar equivalent of H₂ over a Pd catalyst and can then be cleaved by KMnO₄, suggesting it contains a double bond.

Step-by-step explanation:

The student's question is about determining the structure of Compound A (C₆H₁₂) that reacts with hydrogen over a palladium catalyst and then undergoes oxidative cleavage with KMnO₄ in acidic solution to yield certain products.

Considering that Compound A reacts with H₂ to form a compound that upon oxidative cleavage gives products suggests that Compound A has unsaturation (double bond).

Since it reacts with only one molar equivalent of H₂, we can reason that Compound A contains only one double bond.

Cyclohexene is the only compound of the options given with a double bond that could react with H₂ in the presence of a Pd catalyst to add hydrogen across the double bond, making it saturated, and then be subjected to oxidative cleavage with KMnO₄ to yield dicarboxylic acid from the ring.

Therefore, the structure of Compound A based on the information provided is most likely cyclohexene (Option B).