In Section 12.2, we learned that the Simmons-Smith reaction produces a cyclopropane ring from an alkene. Diiodomethane (CH,I2) is treated with a source of zinc to produce the Simmons-Smith reagent (ICH,ZnI), which reacts with the alkene in a single elementary step. Complete the mechanism below by adding the necessary curved arrows for this elementary step. Hint: The curved arrow notation is very similar to that for epoxidation involving a peroxyacid.) H, CH2 Enantiomer + Simmons-Smith reagent

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter9: Alkynes: An Introduction To Organic Synthesis
Section9.SE: Something Extra
Problem 49AP: Occasionally, a chemist might need to invert the stereochemistry of an alkene—that is, to convert...
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In Section 12.2, we learned that the Simmons-Smith reaction produces a cyclopropane ring from an alkene.
Diiodomethane (CH,I2) is treated with a source of zinc to produce the Simmons-Smith reagent (ICH,ZnI), which reacts
with the alkene in a single elementary step. Complete the mechanism below by adding the necessary curved arrows for
this elementary step. Hint: The curved arrow notation is very similar to that for epoxidation involving a peroxyacid.)
H,
CH2
Enantiomer
+
Simmons-Smith reagent
Transcribed Image Text:In Section 12.2, we learned that the Simmons-Smith reaction produces a cyclopropane ring from an alkene. Diiodomethane (CH,I2) is treated with a source of zinc to produce the Simmons-Smith reagent (ICH,ZnI), which reacts with the alkene in a single elementary step. Complete the mechanism below by adding the necessary curved arrows for this elementary step. Hint: The curved arrow notation is very similar to that for epoxidation involving a peroxyacid.) H, CH2 Enantiomer + Simmons-Smith reagent
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