Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 17, Problem 43P
Interpretation Introduction

Interpretation:

The structure of phenacetin and phenetidine from the given data are to be determined.

Concept introduction:

Infrared spectroscopy is a simple, instrumental technique, which helps to determine the presence of various functional groups.

It depends on the interactions of atoms or molecules with the electromagnetic radiation.

Infrared spectroscopy is most commonly used in the identification of the structure of the compound.

Infrared spectroscopy is the examination of the infrared light interacting with a molecule. The examination can be done in three ways, that is, by measuring absorption, emission, and reflection, and it can also measure the vibration of atoms.

Infrared absorption bands indicate the functional groups present in a compound. For example, carbonyl group shows a band from 1600 to 1750 cm-1, hydroxyl group shows a band from 3400 to 3550 cm-1. So, if a compound shows band in the carbonyl range only, it is an aldehyde or ketone; if in the region of hydroxyl, it is alcohol or phenol; if two bands are observed, one in each region, it is a carboxylic acid.

Nuclear Magnetic Resonance (NMR) is one of the most capable analytical techniques used for determining the functional groups and how the atoms are structured and arranged in a molecule.

Few elements, such as 13C and 1H, have nuclei behaving as magnets about an axis. These elements are placed in magnetic field irradiated with electromagnetic energy of specific frequency and the nuclei tend to absorb energy via magnetic resonance. There is this graph that shows energy absorption frequencies and intensities of a sample kept in the magnetic field called nuclear magnetic resonance (NMR).

In NMR spectroscopy, the proton nuclear magnetic resonance (1HNMR) is used to find out the structure of molecules with the help of 1H atom within the molecules.

Induced magnetic field consists of electricity generated from movement in a magnetic field.

Any signal’s position on the X-axis in the NMRspectrum is the chemical shift expressed in δor ppm.

The number of signals in H1 NMRspectrum tells about the number of different chemical environments for the protons.

The area covered by the signal is proportional to the number of equivalent protons causing the signal.

The hydrogen atom on adjacent carbon atoms splits the peak into two or more peaks. One, two, and three hydrogen atoms split the peak into two, three and four peaks, which further, is referred to as doublet, triplet or quartet.

The decrease in the electron density around a proton deshields the signal downfield at a larger value of chemical shift.

The increase in electron density shields the signal upfield at a lower value of chemical shift.

13C NMR is only used in the observation of isotopes of carbon atoms.

NMR data indicates the number and type of protons or carbons present in a compound based on a number of signals obtained in 1H NMR or 13C NMR respectively. 1H NMR signals are often in multiplicity such as doublet, triplets that indicates the number of protons present on the carbons adjacent to that proton. Protons of aromatic ring shows signal from 6.57.5 ppm, those of alkyl group from 0.5 to 1.5 ppm while alkyl groups adjacent to a carbonyl group or oxygen atom show signals from 2.0 to 3.0 ppm. Alcohol group shows a signal at 2.0 to 3.0 ppm but is always a singlet.

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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.
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Chapter 17 Solutions

Organic Chemistry

Ch. 17 - Prob. 11PPCh. 17 - Practice Problem 17.12 What products would you...Ch. 17 - Practice Problem 17.13 (a) Provide the reagents...Ch. 17 - Prob. 14PPCh. 17 - Practice Problem 17.15 Using decarboxylation...Ch. 17 - Practice Problem 17.16 Diacyl peroxides, ,...Ch. 17 - Prob. 17PCh. 17 - Give an IUPAC systematic or common name for each...Ch. 17 - Prob. 19PCh. 17 - Prob. 20PCh. 17 - 17.21 What major organic product would you expect...Ch. 17 - Prob. 22PCh. 17 - Prob. 23PCh. 17 - Prob. 24PCh. 17 - Prob. 25PCh. 17 - 17.26 What products would you expect to obtain...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - 17.28 Indicate reagents that would accomplish each...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - Prob. 30PCh. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - 17.33 On heating,...Ch. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - 17.36 Show how pentanoic acid can be prepared from...Ch. 17 - 17.37 The active ingredient of the insect...Ch. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Give stereochemical formulas for compounds AQ:...Ch. 17 - 17.41 -Glyceraldehyde can be transformed into...Ch. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - 17.44 Given here are the NMR spectra and carbonyl...Ch. 17 - 17.45 Compound Y dissolves slowly when warmed...Ch. 17 - Prob. 46PCh. 17 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Prob. 50PCh. 17 - Prob. 51PCh. 17 - 17.52 Starting with 1-naphthol, suggest an...Ch. 17 - Suggest a synthesis of ibuprofen (Section 5.11)...Ch. 17 - Prob. 54PCh. 17 - Prob. 55PCh. 17 - Prob. 1LGPCh. 17 - Prob. 2LGPCh. 17 - Prob. 3LGPCh. 17 - Prob. 4LGP
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