Packet 2: Tossup 15

Inkster et al. developed a “non-anhydrous, minimally basic” form of this reaction that removes a time-consuming azeotropic-drying step. The 3M company performs this reaction via the CAVE or Simons processes to produce modified inert fluids used to cool electronics. This reaction is performed by the antimony-containing Swarts reagent, as well (10[1])as a DABCO (“dab-ko”) derivative sold by Sigma-Aldrich (10[1])with the prefix “select.” (10[2])This transformation (10[1])is (10[1])performed on aromatic amines via a diazonium salt intermediate in the Balz–Schiemann reaction. (10[2])A 34,000-fold increase in Ka (“K-A”) occurs after this reaction is performed (10[1])three times on (10[1])acetic acid (10[2])due to (10[1])a stronger (10[1])inductive effect. (10[1]-5[2])This reaction is used to generate a PET scan radiotracer from deoxyglucose. (-5[1])For 10 points, name this (10[1])reaction that bonds organic compounds to the lightest halogen. ■END■ (10[8]0[1])

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