ORGO worksheet 22

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

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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 münchnone 1 . (c) What is the hybridization of the ring O, the ring N, and the bold face ring C of 1 ? Some reactions of münchnones 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 münchnone 1 into amidoketene 2 . (e) Is amidoketene 2 a resonance structure of münchnone 1 ? Explain your answer....
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