6. In an organic chemistry lab, chemists were attempting to convert compound I into compound III via a substitution reaction. To their surprise, compound II was the only observed compound after treating compound I with cyanide. :CEN : CN CI CN

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6. In an organic chemistry lab, chemists were attempting to convert compound I into compound III
via a substitution reaction. To their surprise, compound II was the only observed compound after
treating compound I with cyanide.
:CEN :
CN
CI
CN
I3D
observed
II
not observed
a. Provide a detailed, stepwise mechanism for the transformation above that accounts for the
formation of product II. Use the curved arrow formalism to show the flow of electrons. Show
all lone pairs, intermediates, formal charges, and pertinent resonance structures.
b. Explain why product II is formed instead of product III. Use drawings to support your answer.
Transcribed Image Text:6. In an organic chemistry lab, chemists were attempting to convert compound I into compound III via a substitution reaction. To their surprise, compound II was the only observed compound after treating compound I with cyanide. :CEN : CN CI CN I3D observed II not observed a. Provide a detailed, stepwise mechanism for the transformation above that accounts for the formation of product II. Use the curved arrow formalism to show the flow of electrons. Show all lone pairs, intermediates, formal charges, and pertinent resonance structures. b. Explain why product II is formed instead of product III. Use drawings to support your answer.
c. Would you expect compound II to be optically active? Briefly explain. Note: The reaction
above was run on an enantiomerically pure sample of compound I.
CN
II
Transcribed Image Text:c. Would you expect compound II to be optically active? Briefly explain. Note: The reaction above was run on an enantiomerically pure sample of compound I. CN II
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