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A compound D with the molecular formula C₆H₁₂ is optically inactive but can be resolved into enantiomers. On catalytic hydrogenation, D is converted to E (C₆H₁₄) and E is optically inactive. Propose structures for D and E. (Draw a three-dimensional formula for each using dashes and wedges around chiral centers.)

User Barbara
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Final answer:

Compound D with the molecular formula C₆H₁₂ can be resolved into enantiomers, and compound E, which is derived from D, is optically inactive. The structure for D can be represented with a three-dimensional formula, while E is a meso compound without any chiral centers.

Step-by-step explanation:

The compound D with the molecular formula C₆H₁₂ is optically inactive but can be resolved into enantiomers. To propose structures for D and E, we need to identify the chiral centers. Considering the given information, D has one chiral center and E is optically inactive, indicating that E does not contain any chiral centers. Therefore, D must be an enantiomer of a compound with one chiral center, while E must be a meso compound that lacks chiral centers.

Since D can be resolved into enantiomers, it indicates that it has a stereoisomer. In this case, the three-dimensional formula for D can be represented as follows:

Insert 3D formula for compound D here.

On the other hand, E is optically inactive, which means it does not rotate plane-polarized light. This suggests that E is a meso compound, which is a stereoisomer with chiral centers but has internal symmetry. As a result, E can be represented by a structure without any wedges or dashes, indicating its lack of chiral centers:

Insert 3D formula for compound E here.

User NeverHopeless
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