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Chapter 10: Problem 92

\(\mathrm{TCDD},\) or 2,3,7,8 -tetrachlorodibenzo-p-dioxin, is a highly toxic compound It gained considerable notoriety in 2004 when it was implicated in the murder plot of a Ukrainian politician. (a) Describe its geometry and state whether the molecule has a dipole moment. (b) How many pi bonds and sigma bonds are there in the molecule?

Short Answer

Expert verified
The molecule TCDD has a planar geometry and does not possess a dipole moment. It contains 24 pi bonds and 24 sigma bonds.

Step by step solution

01

Determination of Molecular Geometry

TCDD is a planar molecule consisting mainly of carbon and hydrogen atoms along the ring and with chlorine atoms at positions 2, 3, 7, 8. The molecule is symmetrical, and each carbon atom is sp2 hybridized with a trigonal planar geometry.
02

Analysis of Dipole Moment

A molecule has a dipole moment when there is a net imbalance of charge, this usually occurs when there is an unsymmetrical distribution of bonded atoms and lone pairs of electrons around the central atom. Although the C-Cl bonds in TCDD are polar, due to the symmetrical spatial arrangement of these polar bonds, the dipole of each C-Cl bond cancels the others out. Therefore, TCDD does not have a net dipole moment; it is a nonpolar molecule.
03

Calculation of Pi and Sigma bonds

In each carbon atom, one of the three sp2 hybrid orbitals forms a sigma bond with one hydrogen atom/halogen, the second forms a sigma bond with one carbon atom, and the third forms two pi bonds with two carbon atoms. Since there are 12 carbon atoms in this structure, we can conclude that there are 24 pi bonds and 24 sigma bonds in the molecule.

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