Undercover drug enforcement officers purchased a brand spice called \"Don\'t wor
ID: 484473 • Letter: U
Question
Undercover drug enforcement officers purchased a brand spice called "Don't worry, be Happy" from a head shop. Chemical analysis did not indicate the presence of any scheduled controlled substances, but it did provide them with enough evidence to cite the proprietors with unlawful sale of a prescription drug, and to seize all of the remaining stock of Don't Worry Be Happy as evidence. Use the following spectra and chemical test results for the chemical extracted from this spice to determine its structure, and help the D.A. build a case against these semi-legal dope peddlers. Elemental analysis gave an elemental composition of 73.429% carbon, 10.270% hydrogen, with the remainder composed of oxygen. A molecular ion peak could not be observed in the mass spectrum, but the molar mass was found to be 98 g/mole by freezing point depression. One millimole of the compound was found to react with 2 millimoles of bromine in dichloromethane. A) what is the molecular formula of the compound? B) How many degrees of unsaturation does it have? C) How many carbon-carbon pi bonds does it have? D) What two functional groups are indicated in this IR spectrum?Explanation / Answer
a) element C H O
percentage 73.429 10.27 16.301
moles 6.11 10.27 1.01
ratio 6.05 10.16 1
Thus the empirical formula is C6H10O
empirical formula weight = 98
As empirical formula weight = molar mass
empirical formula = molecular formula = C6H10O
b) Degree of unsatration = 1/2 [(6 x2 ) +2 -10]
=2
The two degree of unsaturation is present which may be two double bonds or a triple bonds as one mole of compound reacted with 2 moles of bromine.
c) There are two C-C pi bonds present in the molculle as D.U = 2 and it takes two moles of bromine.
D) The weak band at 2100-2200 shows the presence of -Ctriple bond C - and the broad peak at 3200-3400 shows the presenc eof H- bonded -OH.
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