Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps. Be sure to account for all bond-breaking and bond-making steps. H Select to Add Arrows H :CI: H Select to Add Arrows :J:O Select to Add Arrows CH CFCI: Select to Add Arrows

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps. Be sure to account for all bond-breaking and bond-making steps. H Select to Add Arrows H :CI: H Select to Add Arrows :J:O Select to Add Arrows CH CFCI: Select to Add Arrows

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter5: Resonance

Section: Chapter Questions

Problem 8E

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Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 3390–3400):
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