Furan, \(\mathrm{C}_{4} \mathrm{H}_{4} \mathrm{O},\) is a substance derivable
from oat hulls, corn cobs, and other cellulosic waste. It is a starting
material for the synthesis of other chemicals used as pharmaceuticals and
herbicides. The furan molecule is planar and the \(\mathrm{C}\) and \(\mathrm{O}\)
atoms are bonded into a fivemembered pentagonal ring. The H atoms are attached
to the C atoms. The chemical behavior of the molecule suggests that it is a
resonance hybrid of several contributing structures. These structures show
that the double bond character is associated with the entire ring in the form
of a \(\pi\) electron cloud.
(a) Draw Lewis structures for the several contributing structures to the
resonance hybrid mentioned above.
(b) Draw orbital diagrams to show the orbitals that are involved in the
\(\sigma\) and \(\pi\) bonding in furan. [Hint:
You need use only one of the contributing structures, such as the one with no
formal charges.]
(c) How many \(\pi\) electrons are there in the furan molecule? Show that this
number of \(\pi\) electrons is the same, regardless of the contributing
structure you use for this assessment.