Tropolone \(\left(\mathrm{I}, \mathrm{C}_{7} \mathrm{H}_{7}
\mathrm{O}_{2}\right)\) has a flat molecule with all carbon-carbon bonds of the
same length (1.40 A). The measured heat of combustion is \(20 \mathrm{kcal}\)
lower than that calculated by the method of summing bond energies. Its dipole
moment is \(3.71 \mathrm{D}\); that of 5-bromotropolone is \(2.07 \mathrm{D}\).
Tropolone undergoes the Reimer-Tiemann reaction, couples with diazonium ions,
and is nitrated by dilute nitric acid. It gives a green color with ferric
chloride, and does not react with 2,4 -dinitrophenylhydrazine. Tropolone is
both acidic \(\left(\mathrm{K}_{\mathrm{a}}=10^{-7}\right)\) and weakly basic,
forming a hydrochloride in ether.
(a) What class of compounds does tropolone resemble? Is it adequately
represented by formula I?
(b) Using both valence-bond and orbital structures, account for the properties
of tropolone.
(c) In what direction is the dipole moment of tropolone? Is this consistent
with the structure you have proposed?
(d) The infrared spectrum of tropolone shows a broad band at about \(3150
\mathrm{~cm}^{-1}\) that changes only slightly upon dilution. What does this
tell you about the structure of tropolone?