What is the structure of the compound with the formula C10H14O, if it shows a strong broad IR signal near 3300 cm-1, the 1H-NMR spectrum is: 1.44 ppm (9H singlet) 4.97 ppm (1H broad singlet) 6.90 ppm (2H doublet) 7.32 ppm (2H doublet)

What is the structure of the compound with the formula C10H14O, if it shows a strong broad IR signal near 3300 cm-1, the 1H-NMR spectrum is: 1.44 ppm (9H singlet) 4.97 ppm (1H broad singlet) 6.90 ppm (2H doublet) 7.32 ppm (2H doublet)

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

Chapter17: Carboxylic Acids

Section: Chapter Questions

Problem 17.17P

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Concept explainers

Analyzing and Predicting Spectroscopic Data

The interaction of electromagnetic radiation with the structure of molecules in the sample and their study is referred spectroscopy. Several spectroscopic methods are used to acquire sample information, and these methods are proved to be accurate, fast, and non-destructive. The information obtained about the content and composition of molecules from these spectroscopic methods is called spectroscopic data.

Question

What is the structure of the compound with the formula C₁₀H₁₄O, if it shows a strong broad IR signal near 3300 cm^-1, the ¹H-NMR spectrum is:

1.44 ppm (9H singlet)

4.97 ppm (1H broad singlet)

6.90 ppm (2H doublet)

7.32 ppm (2H doublet)

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