Fluoxymesterone is an anabolic steroid with strong androgenic properties, which has been used for the treatment of hormone-sensitive breast tumors in women. It is also misused as an aggression enhancer in boxing and martial arts competitions. Since the half-life of this hormone in the human body is more than 9h, it can be easily detected in a doping sample taken after the competition. Compare the in-vivo physical properties of both hormones. Which statements below are correct? I) The exchange of a hydrogen atom vs. a fluorine atom does not significantly change the water-solubility, because the C-F bond is short and an organically bound fluorine-atom is almost as small as a carbon-bonded hydrogen atom.
II) The exchange of a hydrogen vs. a fluorine atom does significantly change the water-solubility, because the C-F bond is non-polar covalent, whereas C-H is polar covalent.
III) The introduction of a second hydroxy-group at the C-ring of fluoxymesterone increases the water-solubility.
IV) Fluoxymesterone is less water soluble than testosterone, because it possesses 19 carbon atoms, compared to 19 of testosterone.

Question

Fluoxymesterone is an anabolic steroid with strong androgenic properties, which has been used for the treatment of hormone-sensitive breast tumors in women. It is also misused as an aggression enhancer in boxing and martial arts competitions. Since the half-life of this hormone in the human body is more than 9h, it can be easily detected in a doping sample taken after the competition. Compare the in-vivo physical properties of both hormones. Which statements below are correct?  I) The exchange of a hydrogen atom vs. a fluorine atom does not significantly change the water-solubility, because the C-F bond is short and an organically bound fluorine-atom is almost as small as a carbon-bonded hydrogen atom.
II) The exchange of a hydrogen vs. a fluorine atom does significantly change the water-solubility, because the C-F bond is non-polar covalent, whereas C-H is polar covalent.
III) The introduction of a second hydroxy-group at the C-ring of fluoxymesterone increases the water-solubility.
IV) Fluoxymesterone is less water soluble than testosterone, because it possesses 19 carbon atoms, compared to 19 of testosterone.

Quizplus · Accepted Answer

Statement I is correct. The exchange of a hydrogen atom with a fluorine atom does not significantly change the water solubility, because the C-F bond is short and an organically bound fluorine atom is almost as small as a carbon-bonded hydrogen atom.

Statement II is incorrect. The C-F bond is polar covalent, and thus fluoxymesterone is less water-soluble than testosterone, which contains polar hydroxyl groups.

Statement III is correct. The introduction of a second hydroxy-group at the C-ring of fluoxymesterone increases the water-solubility.

Statement IV is incorrect. Fluoxymesterone has 9 carbon atoms, compared to 19 in testosterone, and the number of carbon atoms is not a significant factor in determining water-solubility.

Fluoxymesterone Is an Anabolic Steroid with Strong Androgenic Properties, Which