This experiment describes a discovery-based method for the regio- and stereoselective hydrochlorination of carvone, appropriate for a 3-h second-semester organic chemistry laboratory. The product is identified through interpretation of the 13C NMR and DEPT spectra are obtained on an Anasazi EFT-60 at 15 MHz as neat samples. A guided-inquiry approach is used to aid the students with the interpretation of the NMR spectra.
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