Question

Now, examine the structures of benzhydrol and fluorene. Both compounds contain the same number of carbons but have very different melting points. At first glance, one might expect benzhydrol to exhibit the higher melting point. Why might one think this?

Answer 1

Answer:

The OH group

Explanation:

Benzhydrol contains OH hydroxyl group in its molecule while fluorene does not. At first glance, one would think that OH, which contributes to hydrogen bonding would causes melting point of benzhydrol to be higher than fluorene. However, the structure of benzhydrol, which is 2 benzene rings connected to center hydroxyl carbon (PhCOHPh), allows for each benzene rings in benzhydrol to rotate until both rings are perpendicular to minimize repulsive force. This prevents the molecule from stacking on each other due to its non flat shape, and thus, lowering its melting point in contrast to flat fluorene molecule.