Question

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.)

Answer 1

D: CH2=CH-CH(CH3)-CH2-CH3 (R & S enantiomers)

E: CH3-CH2-(CH3)-CH2-CH3

(Please see the figures enclosed )

Step-by-step explanation:

D is a racemic mixture (R & S) of 3-metyl-pent-1-ene, so it is optically inactive (although each of two enantiomers is optically active, the mixture is optically inactive. The reason is that two enantiomers are present in an equal amount).

E is optically inactive, so its structure has to be symmetric.