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. "CN observed not observed a. Provide a detailed, stepwise mechaniem 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, intemediates, formal charges, and pertinent resonance structures. b. Explain why product II is formed instead of product III. Use dawings to supportyow 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.

Organic Chemistry
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Author:John E. McMurry
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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.
"CN
observed
not observed
a. Provide a detailed, stepwise mechaniem 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, intemediates, formal charges, and pertinent resonance structures.
b. Explain why product II is formed instead of product III. Use dawings to supportyow 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.
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. "CN observed not observed a. Provide a detailed, stepwise mechaniem 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, intemediates, formal charges, and pertinent resonance structures. b. Explain why product II is formed instead of product III. Use dawings to supportyow 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.
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