H H,C-C=C--CH, 2 H,C-C-C-C-CH, || :0: :O: H :0: H enol form krta form Acetylacetone Co Cr Fe Acetylacetonate complexes (CH;COCHCOCH:JaM where M = Co, Cr, and Fe
The compound whose structure is shown here is acetyl acetone. It exists in two forms:
the enol form and the keto form
The molecule reacts with OH–
to form an anion, [CH3COCHCOCH3
] (often abbreviated
acac
–
for acetylacetonate ion). One or the most interesting aspects of this anion is that
one or more of them can react with
colored compounds
(a) Are the keto and enol forms of acetylacetone resonance forms? Explain your
answer.
(b) What is the hybridization or each atom (except H) in the enol form? What changes
in hybridization occur when it is transformed into the keto form?
(c) What are the electron-pair geometry and molecular geometry around each C atom
in the keto and enol forms? What changes in geometry occur when the keto form
changes to the enol form?
(d) Draw three possible resonance structures for the acac
–
ion.
(e) Is cis-trans isomerism possible in either the enol or the keto form of acetylacetone?
(f) Is the enol form of acetylacetone polar? Where do the positive and negative charges
lie in the molecul
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