Oxygen: The Key to Stereoelectronic Control in Chemistry

Although carbon is considered the central element of organic chemistry, the broader chemical world has one more star player—oxygen. Billions of years of evolution have filled your room with oxygen as countless cyanobacteria and plants work on changing our planet. Oxygen is everywhere—from geology to biology, from the Earth's crust to the ozone layer. This digital primer aims to analyze chemical reactivity through the prism of oxygen chemistry. The key to understanding this chemistry is the lone pairs of oxygen (i.e., the underutilized "idle" electrons that do not directly contribute to the Lewis structure of molecules). By highlighting the many roles of oxygen, we will illustrate how chemistry rises above the limitations of Lewis structures and how electrons stay neither idle nor "lone" even if they are in "lone pairs" when an oxygen atom is near a reaction center. This digital primer will introduce important types of chemical bonding that transcend undergraduate textbooks but that are likely to drive the development of new chemical reactions in the future.