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Question: Phenacetin is an analgesic compound having molecular formula C10H13NO2. Once a commoncomponent in over-the-counter pain relievers such as APC (aspirin, phenacetin, caffeine),phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.

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01

Step-by-Step SolutionStep 1: Phenacetin

Phenacetin was earlier employed as an analgesic and a drug to reduce fever. Today, it is banned as it results in several renal diseases and cancers.

02

 1H   NMR spectroscopy

The information given in an 1H NMR spectra is helpful in predicting the structure of several compounds. The solvents used for analyzing NMR should not possess hydrogen atoms as they may interfere with the spectral analysis

03

IR spectroscopy

IR spectroscopy is also known as 鈥渧ibrational spectroscopy.鈥滻R spectra help recognize the functional groups present in a particular molecule.

04

Deducing the structure of phenacetin from 1H  NMR and IR spectra

The IR absorption at 3300cm-1 and 1680cm-1 indicates the presence of N-H bond and amide linkage. In the NMR data, the triplet at 1.4 indicates the presence of CH3 adjacent to CH2 .The singlet at 2.2 shows the presence of CH3C=Ogroup.

A quartet at 3.9 indicates the presence of CH3 adjacent to CH2 .The doublet at 6.8 indicates two hydrogens on the benzene ring. The singlet at 7.2 shows the presence of NH group.

The doublet at 7.4 indicates the presence of two hydrogens on the benzene ring. The structure of phenacetin can be given as:

Structure of phenacetin

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