Packet L: Tossup 14

A sigmatropic rearrangement follows the addition of these compounds into a nitroarene (“nitro-AIR-een”) in the Bartoli synthesis of 7-substituted indoles. To form cyclopropanols, titanium isopropoxide (“iso-pro-poxide”) first reacts with these compounds in the Kulinkovich reaction. When Keely and Pauson treated cyclopentadiene (“cyclo-penta-diene”) with these compounds followed by iron(III) (“iron-three”) chloride, they unexpectedly made ferrocene instead of fulvalene. Reactions using these compounds often use 1,2-iodoethane to remove an oxide layer. Like Hauser bases, these compounds are treated with dioxane to shift their Schlenk equilibria (10[2])toward (10[2])the (-5[1])halide salt form. (10[1])Carbon-carbon single bonds (-5[1])are formed (10[1])when these compounds (10[1]-5[1])add into carbonyls. (10[3]-5[1])For 10 points, (10[1])name these nucleophilic (10[1])organometallic (10[2])compounds (10[4])with the (10[1])typical (10[2])formula (10[1])RMgX (10[7])■END■ (10[9]0[17])

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