(4 points) The Grob (Wharton) fragmentation involves the reaction of alcohols possessing a leaving group at the It has been shown experimentally

(4 points) The Grob (Wharton) fragmentation involves the reaction of alcohols possessing a leaving group at the It has been shown experimentally that, for the Grob fragmentation to take place, the two breaking bonds (in bold) must be oriented rigidly anti to one another. A) Indicate which of the various stereoisomers of 2 will give 3 by Grob fragmentation. Explain your reasoning. The Key for the chem3D structures is as follows, the oxygen of the hydroxy group is in red, and the bond system that determines whether the reaction will occur and the geometry of the resulting double bond is in blue. If it is unclear from these small pictures, please ask or make the models yourself. B) Indicate which of the various stereoisomers of 2 will give 4 by Grob fragmentation. Explain your reasoning.

 

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