Question
In the Hofmann-Loffler-Freytag reaction, this reaction occurs following the generation of a nitrogen-centered radical. For 10 points each:
[10h] Name this reaction that is often induced by tetrabutylammonium decatungstate (“deca-TUNG-state”). This reaction, which is closely related to PCET reactions, is used to functionalize C-H bonds.
ANSWER: hydrogen atom transfer [or HAT; accept hydrogen atom abstraction; reject “transfer hydrogenation” or “hydrogen transfer”]
[10m] In a reaction of this type, hydrogen is abstracted from tributyltin hydride, and the resulting tributylstannyl (“try-byoot-ill-STAN-ill”) radical attacks a thiohydroxamate (“thigh-oh-high-DROX-uh-mitt”) ester. Halides react with malonic esters via an SN2 reaction in a reaction of this type named for Krapcho.
ANSWER: decarboxylation
[10e] One of the simplest examples of the cleavage of C-H bonds is the halogenation of alkanes, where the halogen radical is generated either via heat or radiation from this region of the electromagnetic spectrum.
ANSWER: ultraviolet light [or UV light; prompt on light]
<Hong, Chemistry>
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