14. - Organic Chemistry (Mcmurry)

Question

Question: Identify each of the colored positions—red, blue, and green—as axial or equatorial. Then carry out a ring-flip, and show the new positions occupied by each color.

Step-by-Step Solution

Answer

The conformation after ring-flip is: 

Chair conformation

Chair conformation structure for six-membered ring is when atoms 2, 3, 5, and 6 lie in the same plane, atom 1 lies above the plane, and atom 4 lies below the plane.

Axial and equitorial positions

Axial bonds are the bonds that are perpendicular or vertical to the ring plane. Equatorial bonds are approximately horizontal in the plane of the ring. 

Ring flip

Ring-flip in chair cyclohexane interconverts axial and equatorial positions. The axial atoms in the starting structure becomes equatorial in the ring-flipped structure, and vice-versa.

Structure before and after ring-flip comparison

Before the ring flip, red  and blue are equatorial and green is axial.

After the ring-flip, red and blue are axial and green is equatorial.