Ring Flip in Organic Chemistry: Definition, Structure & Examples

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

The primary goal of this lesson will be to understand a phenomenon in organic chemistry known as ring flip by studying its definition and looking at specific example structures to illustrate the concept.

Molecules Can Flip Too

Have you ever tried to do a flip? A lot of people are able to do either a back flip or a front flip, especially if they are on a trampoline. Gymnasts are exceptionally good at doing flips and can sometimes complete multiple rotations with or without the aid of a spring board. Doing a flip requires a certain level of confidence and commitment that not all people possess.

Did you know that sometimes organic compounds can actually do flips? It's probably not something everyone appreciates, but nonetheless it's an important concept to be able to understand. In this lesson we will become more familiar with the concept of ring flip by studying its definition and then examining some example structures the help visualize how it works. Let's do some flips!

Definition of Ring Flip

The first important thing to realize is that the concept of ring flip always corresponds to to cyclohexane ring systems. A cyclohexane ring is a six-membered carbon ring that can be substituted with all hydrogen atoms or other non-hydrogen substituents. The other important thing we need to realize is that because of the atoms of cyclohexane wanting to maximize distance between one another, the molecule adopts what's called a chair conformation as its lowest energy conformation.

Chair conformation of cyclohexane

The red and blue bond colors on the chair structure of cyclohexane correspond to the two different bond positions in cyclohexane. The red bonds represent what are called axial bonds (above and below the plane of the ring) and the blue bonds correspond to equatorial bond (around the equator or belt of the ring) positions.

When a cyclohexane ring undergoes a ring flip, the carbon with a gray circle folds up and the carbon labeled with a blue circle folds up. The result is the flipped version of the cyclohexane ring.

Example of a cyclohexane ring undergoing a ring flip

Structural Examples of Ring Flip

Now that we're familiar with the concept of ring flip let's take a look at some structures to serve as specific examples. Consider the structure 1-methylcyclohexane as our first case, a simple cyclohexane system with a methyl group as a substituent. In the chair structure on the left the methyl group is in an axial bonding position but once the ring flip happens, the methyl group moves to an equatorial bond position. This is an important realization, that if a substituent is in an axial position in one chair structure it will move to an equatorial position after the ring flip. Note how the hydrogen atoms labeled in pink also switch positions.

Ring flip of 1-methylcyclohexane

What about a cyclohexane system with two non-hydrogen substituents like 1-bromo-4-methylcyclohexane? In the chair structure to the left of the arrows the bromine atom is occupying an axial bond position (pointing up) and the methyl group is in an equatorial bond position (also pointing up).

The two chair structures of 1-bromo-4-methylcyclohexane

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