Question: Many drugs are sold as their hydrochloride salts , formed by reaction of an amine with HCl.
a. Draw the product (a hydrochloride salt) formed by reaction of acebutolol with HCl. Acebutolol is a blocker used to treat high blood pressure. b. Discuss the solubility of acebutolol and its hydrochloride salt in water. c. Offer a reason as to why the drug is marketed as a hydrochloride salt rather than a neutral amine.
b. The neutral form of acebutolol has five functional groups to bond hydrogen with water molecules. Therefore, it is soluble in water. The hydrochloride form of acebutolol is highly soluble in water.
c.Due to the great solubility in water, the hydrochloride salt of acebutolol is injected directly into the bloodstream for quick effect.
Compounds containing ionic bonds are rapidly broken in the water. Therefore, the salts are more soluble in water.
The reaction of an acid with a base gives a salt in which the cation part of the acid and anion part of the base results in its formation.
a. The reaction of acebutolol with HCl gives a hydrochloride salt of acebutolol. The stronger base in the acebutolol is the secondary amine, which is free to abstract the proton from an acid. The other amine group is in conjugation with the carbonyl group. Therefore, the lone pair of electrons is not free for this amine.
Formation of hydrochloride acebutolol salt
b. The hydrochloride salt of acebutolol is more soluble in water because it has an ionic bonding. It rapidly dissolves in water due to the ionization of hydrochloride salt. The neutral form of acebutolol has only hydrogen bonding. Therefore, it slowly dissolves in water or is less soluble than its salt.
c. The hydrochloride salt of acebutolol is marketed due to its high solubility in water. Therefore, the drug is injected directly into the bloodstream for a great and rapid effect.
Question: Cocaine is a widely abused, addicting drug. Cocaine is usually obtained as its hydrochloride salt (cocaine hydrochloride) but can be converted to crack (the neutral molecule) by treatment with base. Which of the two compounds here has a higher boiling point? Which is more soluble in water? How does the relative solubility explain why crack is usually smoked but cocaine hydrochloride is injected directly into the bloodstream?
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