6 The cyclobutadiene molecule (C4H4) deviates high-symmetry square geometry to c

Question

6 The cyclobutadiene molecule (C4H4) deviates high-symmetry square geometry to compensate for its antiaromatic from a synthesized. electronic structure. A silicon analog of diene, called Si was recently The air- and moisture-sensitive, orange, crystalline compound is stabilized by bulky 1.1.7.7- (EMind) groups. x-ray crystallographic analysis of the compound reveals alternating pyramidal and planar configurations at the silicon atoms in the four-membered Also, there are two peaks, separated by >350 the 20si spectrum the compound which ppm, in NMR of suggests a contribution of an alternately charge-separated structure. Me EMind EMind, e EMind Et e EMind SL(EMind) EMind (a) Based on the data disclosed above, circle the resonance form that is the major contributor to the actual structure of Si(EMind) (0.1 pt) (b) Put astricks ()next to the silicon atoms that are responsible for the most downfield peak in the 20Si NMR spectrum. (o 1 p) (c) Should Si(EMind)4 be considered antiaromatic? Why or why not? (0.2 pts)

Explanation / Answer

a) resonance form of structure is the one at the centre. with charges on Si atoms

b) Si+ atoms are responsible downfield signal.

c) Yes. it can be considered as anti-aromatic because there are 4pi electrons in the ring. The 4n rule. For aromatic compounds the rule is 4n+2 pi electrons.

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