MCAT General Chemistry Review

Chapter 10: Acids and Bases

Introduction

Some medications can be applied as drops, salves, or creams to mucous membranes. Others are injected. Some employ a transdermal patch, while others are swallowed or inhaled. The route of administration of a drug compound is related to both the location of its target tissue (local or systemic), as well as the chemical and physical properties of the compound. For example, compounds that are water-soluble can be administered intravenously (an aqueous solution dripped directly into the bloodstream), while those that are lipid soluble can be administered transcutaneously (via a patch or a cream) or orally (in a pill or liquid suspension). The polarity, size, and charge of the drug compound will determine its solubility in polar or nonpolar environments and will be major contributing factors in determining the most effective and efficient route of administration.

Whether a drug compound has an ionic charge is usually a function of the acidic or basic nature of the compound. For example, a basic organic compound that is insoluble in water when neutral can be reacted with an acid to form a salt; because this salt is ionic, it is water-soluble. Correspondingly, an acidic organic compound that is insoluble in water when neutral can be reacted with a base to form a water-soluble salt. On the other hand, the protonated (acidic) form of an organic compound can be reacted with a base to neutralize the compound and release it from its salt, changing (and usually reversing) its solubility in water.

Medical professionals aren’t the only ones concerned about drug solubilities and routes of administration—there’s a science to illicit drugs, too. One of the clearest examples of this is the difference between the two major forms of cocaine, a large alkaloid compound derived from the coca plant. Today, cocaine is used primarily in two different forms. Most commonly, the alkaloid compound is reacted with hydrochloric acid (which protonates its tertiary amine functional group), extracted with water, and dried to a water-soluble powder (cocaine hydrochloride); this powder either is snorted (insufflated) into the nasal cavity, where it is absorbed into the capillary beds, or is injected directly into the venous circulation. The salt form has a very high boiling point, which is close to the temperature at which cocaine degrades, and cannot be smoked. To produce a vaporizable form of cocaine that can be inhaled from a pipe, the cocaine hydrochloride must be reacted with a base, typically either ammonia (to produce pure freebase cocaine) or sodium bicarbonate (to produce the less-pure crack cocaine). The base reacts with the protonated tertiary amine, removing the hydrogen ion to reform the neutral alkaloid compound. The freebase cocaine is water insoluble and usually extracted with ether, or it is left in the aqueous solution, which is heated and evaporated. The freebase and crack forms of cocaine have much lower boiling points; consequently, they can be smoked without risk of degradation.

In this chapter, our focus will be those two classes of compounds—acids and bases—that are involved in so many important reactions. Acid–base reactions are an important topic for the MCAT; in fact, neutralization reactions are some of the most commonly tested reaction types on Test Day. We will begin with a review of the different definitions of acids and bases and their properties, including the characterization of acids and bases as either strong or weak. Focusing on weak acids and bases, we will discuss the significance of the equilibrium constants Ka and Kb for acids and bases, respectively. Finally, we will review acid–base titrations and buffer systems.