ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY.
ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY.
4th Edition
ISBN: 9781119832638
Author: Klein
Publisher: WILEY
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Chapter 17, Problem 59IP
Interpretation Introduction

Interpretation: From the given data of IR spectrum, 1HNMR spectrum and 13C NMR spectrum of the given molecular formula, structure of the compound should be given.

Concept introduction:

  • In the IR spectrum, the signal just above 3000 cm-1 confirms the presence of  aromatic ring
  • Aromatic compound also produces a series of signals between 1450 and 1650 cm-1 in the IR spectrum
  • In the 1HNMR spectrum, the signals between 6.5 and 8ppm confirms the aromatic ring. The presence of a multiplet near 7 ppm is one of the best way to verify the aromatic ring
  • In the 1HNMR spectrum,  the singlet at 3.9ppmwith an integration of 3 represents a methyl group and  the singlet at 2.6ppm with an integration of 3 represents an isolated methyl group
  • The integration value of the multiplet near 7ppm indicates the extent of substitution. An integration  of 5 indicates monosubstituted ring, an integration of 4 indicates disubsituted ring
  • The carbon atoms of aromatic rings typically produce signals in the range of 100-150ppm in 13C NMR spectrum. The number of signals is very helpful in determining the specific substitution for substituted aromatic ring.
  • HDI Calculation:

    HDI=2(C)+2+N-H-X2whereCrepresentthenumberofcarbonNrepresentthenumberofnitrogenHrepresentthenumberofhydrogenXrepresentthenumberofhalogen.

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