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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 observed not observed

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 observed not observed

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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 II 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
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 II 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
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