MCAT Organic Chemistry Review

Nomenclature

Introduction

You walk into the pharmacy looking for something to take for a headache and find an entire aisle of drugs just for that purpose: Advil, Aleve, Motrin, Tylenol, ibuprofen, naproxen, acetaminophen, and aspirin. In this list, however, there are only four distinct drugs. In the United States, it is not uncommon for drugs to be known by both generic and brand names—and sometimes, multiple brands market the same medications. As a medical student, you’ll have to know both: while a doctor may order atorvastatin 40 mg qd, patients will tell you they’re taking Lipitor daily.

For doctors, a generic name is sufficiently unambiguous to specify a given compound, but this is not true within the pharmaceutical industry. Medications are usually large organic compounds with many functional groups and numerous chiral centers. Chemists needed to be able to describe such compounds, as well as innumerably many others. Thus, within chemistry, a specific set of rules for naming and describing compounds was designed. In this chapter, we’ll examine the steps for naming a compound and then practice applying them to example compounds. By the end of the chapter, we’ll have discussed the most common functional groups for Test Day and how they relate to each other in the nomenclature hierarchy. Note that you may have learned nomenclature for a number of other compounds, including ethers, epoxides, amines, imines, sulfonic acids, and others in your organic chemistry courses; we have restricted the content of this chapter to only the functional groups you are expected to know on Test Day.