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Organic Chemistry 1

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Moderate

Structure of a Controlled Substance from IR, Mass Spec and NMR

ORGO1-EXRFQS

During the raid of a clandestine lab, a clear oil compound was found. This oil has a very strong and persistent odor that is difficult to remove from walls, carpets, clothing, or skin. It was suspected to be a Schedule II controlled substance. This compound was taken to a forensic lab, and the following spectroscopic data were obtained.

Determine the structure of this compound.

Mass Spectrum (Electron Impact Ionization). Adapted from NIST Chemistry WebBook: NIST Mass Spec Data Center, S.E. Stein, director, "Infrared Spectra" in NIST Chemistry WebBook, NIST Standard Reference Database Number 69, Eds. P.J. Linstrom and W.G. Mallard, National Institute of Standards and Technology, Gaithersburg MD, 20899, http://webbook.nist.gov, (retrieved June 23, 2016).

Infrared Spectrum. NIST Mass Spec Data Center, S.E. Stein, director, "Infrared Spectra" in NIST Chemistry WebBook, NIST Standard Reference Database Number 69, Eds. P.J. Linstrom and W.G. Mallard, National Institute of Standards and Technology, Gaithersburg MD, 20899, http://webbook.nist.gov, (retrieved June 23, 2016).

${ }^{ 1 }$HNMR Spectrum. Created for Albert.io. Copyright 2016. All rights reserved.

A

Created for Albert.io. Copyright 2016. All rights reserved.

B

Created for Albert.io. Copyright 2016. All rights reserved.

C

Created for Albert.io. Copyright 2016. All rights reserved.

D

Created for Albert.io. Copyright 2016. All rights reserved.