Pyridinium chlorochromate, or PCC, is a reagent that can perform a mild type of this reaction. For 10 points each:
[10e] Name this type of reaction exemplified by the conversion of an alcohol to a carbonyl group, such as in one named for Jones. This type of reaction corresponds to a loss of electrons.
ANSWER: oxidation [accept Jones oxidation]
[10m] This oxidation converts an alcohol to a carbonyl using oxalyl chloride in an “activated DMSO” reaction. The notoriously odorous dimethyl sulfide is produced as a byproduct of this reaction.
ANSWER: Swern oxidation
[10h] The Corey–Kim oxidation uses dimethyl sulfide and a chlorine derivative of this compound. Bromine radicals used for allylic bromination come from a derivative of this compound in the Wohl–Ziegler reaction.
ANSWER: succinimide [or N-chlorosuccinimide or N-bromosuccinimide; prompt on NCS or NBS]
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