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Solved: The 1H NMR spectra of three isomers with molecular

Chapter 15, Problem 58P

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QUESTION:

The \({ }^{I} H\ N M R\) spectra of three isomers with molecular formula \(\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}\) are shown here. Which isomer produces which spectrum?

Equation Transcription:

Text Transcription:

^I H NMR

C_7 H_14 O

Questions & Answers

QUESTION:

The \({ }^{I} H\ N M R\) spectra of three isomers with molecular formula \(\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}\) are shown here. Which isomer produces which spectrum?

Equation Transcription:

Text Transcription:

^I H NMR

C_7 H_14 O

ANSWER:

Solution 58P

(a) From the 1H NMR spectrum, the 9 protons give only one signal at 0.94 ppm because of this reason the three methyl groups are bonded to one carbon.

The 3 protons give one signal at 2.13 ppm because of this reason the methyl group is bonded to carbonyl group. The 2 protons give one signal at 2.37 ppm because of this reason the methylene group is bonded to carbonyl group and tertiary butyl carbon.

Therefore, the isomer, 4,4-dimethyl-2-pentanone produces the below spectrum.

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