Organic chemistry molecular modeling/analysis question. Attached is the 3D molec

Question

Organic chemistry molecular modeling/analysis question. Attached is the 3D molecule image and a literature image of the molecule. Please answer all three questions.

Is the molecule planar or non planar? Explain why the molecule adopts the conformation you See. What geometric parameter tells you whether the atoms are in the same plane, explain? Do you expect delocalization of electrons between the two phenyl rings in the above compound (complete delocalization of electrons over the entire molecule )?Explain

Explanation / Answer

The molecule is not planar.

The molecule adopts this conformation because the steric interactions are less in this conformation. The phenyl and the anthracene group are as far apart as possible, resulting in minimal steric interactions.

2. The bond lengths can help us determine if all atoms are in same plane.

If the molecule is planar, then there would be delocalization of electrons over entire molecule and all bonds would be of same length. If all bonds are found to have same bond length, the molecule would be planar.

3. Since, the molecule is not planar, there would be not be complete delocalization of electrons over entire molecule. The electrons in the phenyl ring are delocalized over 6 atoms of the benzene ring. The electrons in the anthracene group are also delocalized over the 14 carbons of anthracene but there is no complete delocalization over entire molecule due to lack of planarity of the molecule.

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