Question

fat/oil solubility of heroin
using the information on
hydrogen bonding from your
previous answer, which would be
the most fat/oil soluble of the
three below? (hint: it will be the
one thats the least water
soluble.)
the bbb is like an oil/fat:
soluble in oil/fat soluble in water
not dipoles dipoles
limited or no
hydrogen bonding
ability many oh groups
for hydrogen
bonding
long chain of
carbons and
hydrogens like oil
oxycodone morphine heroin

Explanation:

According to the hint, the most fat/oil - soluble compound is the least water - soluble. Heroin has limited or no hydrogen - bonding ability (compared to oxycodone and morphine which have \(OH\) groups for hydrogen bonding). Oxycodone has two \(OH\) groups (which can participate in hydrogen bonding with water), morphine has three \(OH\) groups (more hydrogen - bonding ability with water). Heroin has ester groups (\(-COO-\)) instead of many \(OH\) groups. Since substances with limited hydrogen - bonding ability are less water - soluble and more likely to be fat/oil soluble (based on the principle that non - polar or less polar substances dissolve in non - polar (oil/fat) solvents), and the structure of heroin shows it has less capacity for hydrogen bonding (as per the comparison of functional groups with oxycodone and morphine).

Answer:

Heroin