Question

The unlikely representation(s) of resonating structures of fluorobenzene is:

a)

b)

c) 

d) 

Answer 1

Hint: Fluorobenzene shows resonating structures because it has overlapping orbitals. The overlap of 2p orbitals forms the double bond or the pi bonds in which the resonance occurs.
Complete step by step answer:
1.) Resonance structures are an alternating method or way of drawing a Lewis-dot structure for a compound. Resonance structure is defined as two or more possible structures of any compound. These structures have the identical geometry but different arrangements of the paired electrons. Thus, we can say that resonating structures are just a way of representing the same molecule in different structures.
2.) Fluorobenzene has the following resonating structures:

3.) The Resonance structures of fluorobenzene involve the imaginary movement of pi-bonded electrons or of lone-pair electrons that are adjacent to (i.e. conjugated to) pi bonds.
4.) We can never shift the location of electrons in sigma bonds – if we show a sigma bond forming or breaking, then it is a chemical reaction. Likewise, the positions of atoms in the molecule cannot change between two resonance contributors.
5.) The pi-bonded electrons shift along the ring causing the carbon atom with an excess of an electron and fluorine with a deficiency of an electron. Thus, the fluorine atom will have a positive charge showing the electron deficiency and the carbon atom in the ring will have a negative charge showing an excess of electron.
6.) This suggests that the fluorine atom can never have a negative charge and hence such resonating structures are not possible.

Therefore, the resonating structures of fluorobenzene shown in options (c) and (d) are not possible.

Note: The below resonating structures of fluorobenzene seem same but are different when drawing the resonating structures in a way that there are two ortho carbons in fluorobenzene, so we have to show a resonating structure showing the charge delocalization to each ortho carbon.