Draw the structure of a compound with molecular C₈H₁₄ that reacts with one equivalent of H₂ over Pd/C to form a meso compound

Verified step by step guidance

1. Step 1: Analyze the molecular formula C8H14. The degree of unsaturation can be calculated using the formula: \( ext{Degree of Unsaturation} = rac{2C + 2 - H}{2} \). For C8H14, \( ext{Degree of Unsaturation} = rac{2(8) + 2 - 14}{2} = 2 \). This indicates the presence of two double bonds, one triple bond, one ring and one double bond, or two rings in the structure.
2. Step 2: The problem states that the compound reacts with one equivalent of H2 over Pd/C to form a meso compound. This suggests that the compound contains a single double bond that can be hydrogenated, and the resulting product must have a plane of symmetry (a characteristic of meso compounds).
3. Step 3: To form a meso compound upon hydrogenation, the starting compound must have a symmetrical structure. A likely candidate is a compound with a double bond in a symmetrical position, such as a cis-alkene in a cyclic structure (e.g., a cycloalkene).
4. Step 4: Consider a symmetrical cyclic structure with one double bond, such as 1,2-cyclooctadiene. Upon hydrogenation, the double bond is reduced, and the resulting compound (cyclooctane) is meso because it has a plane of symmetry.
5. Step 5: Draw the structure of the compound. The starting compound is a symmetrical cycloalkene (e.g., cis-1,2-cyclooctadiene), and the product after hydrogenation is a meso compound (cyclooctane). Ensure the double bond is placed in a position that maintains symmetry in the starting structure.

Key Concepts

Molecular Formula and Structure

The molecular formula C8H14 indicates a compound with eight carbon atoms and fourteen hydrogen atoms. Understanding how to derive the structural representation from this formula is crucial, as it helps in visualizing the compound's connectivity and functional groups. The structure must also accommodate the reactivity with hydrogen, suggesting the presence of unsaturation, such as double bonds or rings.

Hydrogenation Reaction

Hydrogenation is a chemical reaction where hydrogen (H2) is added to a compound, typically in the presence of a catalyst like palladium on carbon (Pd/C). This process is essential for converting unsaturated compounds into saturated ones. In this case, the reaction with one equivalent of H2 implies that the compound has at least one double bond that can be reduced, leading to the formation of a meso compound.

Meso Compounds and Symmetry

Meso compounds are achiral molecules that contain multiple stereocenters but possess an internal plane of symmetry. This symmetry allows for superimposition of the molecule on its mirror image, which is a key characteristic of meso compounds. When drawing the structure, it is important to ensure that the resulting product after hydrogenation exhibits this symmetry, confirming its classification as a meso compound.