ORGO worksheet 22

ORGO worksheet 22 - (b) Use the arrow formalism to write...

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Problem 22, Chemistry 301X- 2006 “Münchnones” 1 belong to a class of compounds known as mesoionic compounds, which cannot be satisfactorily represented by Lewis structures not involving charge separation. Münchnones were first investigated at the University of Munich, hence the name. N C C O C O R R R "R" means "anything" - you need not worry about the structure of R 1 (a) Write a Lewis dot structure for münchnone 1 . That is, fill in the missing electron pairs.
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Unformatted text preview: (b) Use the arrow formalism to write six additional resonance structures for mnchnone 1 . (c) What is the hybridization of the ring O, the ring N, and the bold face ring C of 1 ? Some reactions of mnchnones 1 are thought to proceed through the amidoketene 2 . N C R R C O R C O 2 (d) Use the arrow formalism to convert mnchnone 1 into amidoketene 2 . (e) Is amidoketene 2 a resonance structure of mnchnone 1 ? Explain your answer....
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