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Question: The low-resolution mass spectrum of an unknown analgesic X had a molecular ion of 151. Possible molecular formulas include C7H5NO3, C8H9NO2, and C10H17N. High-resolution mass spectrometry gave an exact mass of 151.0640. What is the molecular formula of X?

Short Answer

Expert verified

Answer

The molecular formula of the unknown analgesic X is C8H9NO2

Step by step solution

01

High-resolution mass spectrometry

Spectrometry using high-resolution mass spectrometers to find the accurate molecular weight of a compound is called HRMS.

In this method, the formula mass is calculated with accuracy up to 4 decimal places.

It is extensively used in drug analysis to find the exact chemical composition of drugs.

02

Predicting molecular formula using HRMS

The mass spectrum of a compound gives the m/z value of the molecular ion which can be used to find the molecular mass.

The molecular mass of a compound can also be obtained by adding the exact masses of all the atoms present in the compound. Then, this molecular mass can be compared to the molecular mass from the mass spectrum to find the molecular formula of the unknown compound.

03

Step 3:

The exact mass of analgesic as obtained from the mass spectrum is 151.0640.

The exact masses of carbon, hydrogen, nitrogen, and oxygen are 12.0000, 1.00783, 14.0031, and 15.9949 respectively.

Therefore,

The exact mass of C7H5NO3can be given as:

mC7H5NO3=(7×12)+(5×1.00783)+(1×14.0031)+(3×15.9949)=151.0270

The exact mass of C8H9NO2can be given as:

mC8H9NO2=(8×12)+(9×1.00783)+(1×14.0031)+(2×15.9949)=151.0634

The exact mass of C10H17Ncan be given as:

mC10H17N=(10×12)+(17×1.00783)+(1×14.0031)=151.1362

The exact mass of X is closest toC8H9NO2.

Hence, the molecular formula of analgesic is C8H9NO2.

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Most popular questions from this chapter

Question: Benzene, toluene, and p-xylene (BTX) are often added to gasoline to boost octane ratings. What would be observed if a mixture of these three compounds were subjected to GC–MS analysis? How many peaks would be present in the gas chromatogram? What would be the relative order of the peaks? What molecular ions would be observed in the mass spectra?

Question:Propose a structure consistent with each set of data.

a. a compound that contains a benzene ring and has a molecular ion at m/z= 107

b. a hydrocarbon that contains only sp3 hybridized carbons and a molecular ion at m/z= 84

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Question:Primary (1°) alcohols often show a peak in their mass spectra at m/z= 31. Suggest a structure for this fragment.

Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has a molecular ion in its mass spectrum at 154 and a strong peak in its IR spectrum at 1730 cm-1. Without added NaOCOCH3, oxidation of citronellol with PCC yields isopulegone, which is then converted to B with aqueous base. B has a molecular ion at 152, and a peak in its IR spectrum at 1680 cm-1.

a. Identify the structures of A and B.

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c. Draw a mechanism for the conversion of isopulegone to B.

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