Question

Compound j is optically active and has the molecular formula c6h10 and has a four carbon ring. on catalytic hydrogenation, j is converted to k (c6h12) and k is optically inactive. propose structures for j and k. (draw a three-dimensional formula for each using dashes and wedges around chiral centers.) j (draw one of the enantiomers):

Answer 1

Compound J, with the formula C6H10, could be a cyclobutane with two methyl groups creating a chiral center, which becomes a non-chiral cyclohexane (C6H12) upon hydrogenation.

Step-by-step explanation:

The student's question is related to the identification of the structures of an optically active compound with the molecular formula C6H10, and its hydrogenated form C6H12.

Compound J must be a cycloalkane with a four-carbon ring to fit the given molecular formula and to be optically active, it should contain at least one chiral center. Given that hydrogenation leads to an optically inactive compound (K), it suggests that compound J had one or more chiral centers which become quenched upon hydrogenation.

One possible structure for J could be a cyclobutane ring with two methyl groups bonded to adjacent carbon atoms, creating a chiral center at one of those carbons. Upon hydrogenation, the double bonds are saturated, resulting in a compound with all single bonds, thus removing any chirality and creating an optically inactive compound (K).

The proposed structure for J could be represented as follows (for one of the enantiomers):

• Cyclobutane ring with a chiral center (drawn using dashes and wedges).
• Two methyl groups (-CH3) attached to adjacent carbons.

And for compound K, after hydrogenation:

• Cyclohexane (since the addition of H2 would give us C6H12, which is the formula for cyclohexane).
• No chiral centers as all carbons are in the plane of symmetry.