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https://images.squarespace-cdn.com/content/v1/5afc383d3917eeaa01fce238/1551799338827-DH63HDHA6LSNGC5DZDNR/IMG_1287.jpg Archive https://images.squarespace-cdn.com/content/v1/5afc383d3917eeaa01fce238/1548954372305-8M9KBJ43CCB2P0WAY9Z7/Screen+Shot+2019-01-31+at+11.05.57+AM.png Archive An interesting synthesis of seven membered carbocycles from readily available chemical building blocks was reported in 1986. MeMgBr was added to the cyclopropane hemiketal, then the cyclohexane enolate (2 eq.) was added via cannula to the reaction. Please identify the mechanism of this transformation and provide a transition state of the key intermediate that explains the stereoselectivity and reactivity observed in this reaction https://images.squarespace-cdn.com/content/v1/5afc383d3917eeaa01fce238/1549380074564-HYKJHOFI30P75P5HQB2K/Screen+Shot+2019-02-05+at+9.11.41+AM.png Archive SOLUTION https://images.squarespace-cdn.com/content/v1/5afc383d3917eeaa01fce238/1548953943372-TC101YLKMGET67521VKH/image.png Archive In a classic thermal transformation the acyl azide above was heated in the presence of butanol to afford a 1:1 mixture of diastereomers. Later studies determined that the enantiomerically pure starting material above provides each diastereomer enatiomerically pure. 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