Chapter 4, Problem 4.15YT

Interpretation Introduction

Interpretation:

Using a molecular modeling kit, a model of cyclohexane is to be constructed and viewed so that it looks just like the structure on the left in Figure 4-20. A chair flip is to be performed by moving the two carbon atoms indicated by the red arrows to obtain the conformation on the right in the figure. This procedure is to be reversed and repeated several more times. As you flip the chair back and forth, the bonds of the ring that rotate and the directions in which they rotate are to be identified. Those bonds in the drawing on the left in Figure 4-20 are to be circled and labeled.

Concept introduction:

When we build the cyclohexane model, make sure to include all $\text{C-C}$ and $\text{C-H}$ bonds. All of the C-C bonds undergo rotation in the opposite direction. A chair flip converts axial hydrogen into equatorial hydrogen and vice versa.