Question

An interesting atmospheric molecule that has attracted much recent attention is H COO. This molecule is sometimes called the Criegee intermediate, named after German Organic Chemist Rudolf Criegee. It is formed by reactions between ethene with ozone, and has been found to play an important role in many atmospheric reactions. a. Write down the Lewis structure for this molecule. This molecule has the same number of electrons (iso-electronic) with ozone (Os, O-O-O), which can be used to help determining the Lewis structure. :0: tCO-H b. Predict possible resonance structures for this molecule, and calculate the formal charge of the C O atoms in all resonance structures. H-C-- Based on the resonance structures, can you predict whether the bond lengths of the O-0 and O- C bonds are larger or smaller than the corresponding single bonds? c. d. Based on your Lewis structures, can you predict the geometries of the C and the central O? e. (Extra credit) In addition to the zwitterionic, namely with two charges in opposite signs, resonance structures, the Criegee intermediate can also have the so-called biradical, namely with two unpaired electrons, resonance structure, in which the C and terminal O each has an unpaired electron. Can you figure out the biradical structure?

Answer 1

Please find all the answers (a, b, c, d, and e) for the Criegee intermediate H₂COO as below two images.

Date a) Lewis structure of the molecule cu Coo) +6) Possible resonance structure for H Cero 7 ac AG Based on the resonane soneture are as below - theoretical valves. Bond length c=01 - 1.293 4 o=0 = 1.210 A co - 1.4304 0-0 = 9.352A There are the bond length of the 0-0 and o-c. bands are smaller than the corresponding Single bonds I

Based on the leweis structure de geometzy a carbon and the central oxyge batom very have sp2 hybridization alome e) the biradical stoneture of 4000 is