Problem 11 (50 points) DEA agents raided a building that was suspected to be a c

Question

Problem 11 (50 points) DEA agents raided a building that was suspected to be a clandestine laboratory for the manufacture of illicit drugs. In the raid they confiscated several 4 liter bottles, marked simply good stuff, which contained an acrid smelling oily liquid. Even before an elemental analysis could be performed, rapid spectroscopic tests provided sufficient evidence to arrest the proprietors for conspiring to manufacture a controlled substance. These are the spectra of the mystery material. Your job (if you are willing to accept it) is to go step by step and determine its chemical structure. This paper will spontaneously combust in 10,9, 8 Mass Spectrum at ion (Mass of 198) 40 20 40 60 80 100 120 140 1600 180 200 A) (4 points) Upon review of the spectrum the presence ofan element that is neither hydrogen nor carbon is immediately obvious, What is that element and what peaks indicate it's presence

Explanation / Answer

a) Revies of mass spectrum shows that

molecular ion peak is at 200

loss of 81(M-81 ) is the next peak at 119.

Loss of 81 corresponds to Br , thus the extra element the molecule has is Br.

b) The peak at 119 indicates loss of Br

c) the fragement responsible for the base peak is stable benzylic ion (m/e=91) which can rearrange to stable tropylium ion (m/e91).

d) The functional group present in this molecule is a carbonyl group . loss of 28 units leads fron peak 119 to to peak 91.

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