Chapter 4.3, Problem 4P

Interpretation Introduction

Interpretation:

The plane of symmetry is to be located in $\text{trans-1,3-cyclobutanediol}$. It is to be determined whether $\text{cis-1,3-cyclobutanediol}$ possesses a center of symmetry or a plane of symmetry. It is to be specified whether $\text{cis-1,3-cyclobutanediol}$ is chiral or achiral.

Concept introduction:

A chiral carbon atom is attached to four different atoms or groups of atoms.

In case of cyclic compounds, the chirality center is the carbon which is attached to two different groups, and the sequence of atoms around the ring from that carbon in clockwise direction must be different than that in counter clockwise direction.

A plane of symmetry bisects a molecule in two equal halves, which are mirror images of each other.

If a molecule possesses a center of symmetry or a plane of symmetry, it is superimposable on its mirror image. Then it is said to be an achiral molecule.

If a molecule has at least one chiral carbon atom and no elements of symmetry, then it is said to be a chiral molecule.