Answered: 100- "H NMR (phenacetin) 3H 3H 50- 2H…

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100- "H NMR (phenacetin) 3H 3H 50- 2H 2H 2H 4000 3500 3000 2500 2000 1500 1000 500 Wavenumber (cm") % Transmitance

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.26P

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

Phenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-thecounter 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.

100-
"H NMR (phenacetin)
3H
3H
50-
2H 2H
2H
4000
3500
3000
2500
2000
1500
1000
500
Wavenumber (cm")
% Transmitance

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