Analyze the structure of cocaine and cocaine hydrochloride and determine which is more soluble in water and fat.
Recall that water (H2O) is a polar molecule that exhibits hydrogen bonding and dipole-dipole interactions. Using the concept of like dissolves like, we can determine which solvent is better for both compounds
The "free-base" form of cocaine (C17H21NO4) and its protonated hydrochloride form (C17H22ClNO4) are shown below; the free-base form can be converted to the hydrochloride form with one equivalent of HCl. For clarity, not all the carbon and hydrogen atoms are shown; each vertex represents a carbon atom with the appropriate number of hydrogen atoms so that each carbon makes four bonds to other atoms.
One of these forms of cocaine is relatively insoluble in water: which form, the free base or the hydrochloride?
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