Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 13.12, Problem 20P
Interpretation Introduction

Interpretation:

The structure of an alcohol of given molecular formula C4H10O to be predicted using 13CNMR spectra.

Concept introduction:

The 13CNMR spectrum gives information on the different electronic environments of carbon. As like 1HNMR, the number of signals generated in 13CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring 13C-13 C nuclei are weakly involved due to the low abundance of 13C isotopes of carbon atom.

To Identify:

The structure of an alcohol of given molecular formula C8H16O.

Broadband-decoupled 13CNMR spectrum:

The spectra provide information regarding the total number of carbon environments.

DEPT (Distortionless enhancement by polarization transfer):

a) DEPT-90: The spectrum exhibits signal only from CH group and no signals from CH3, CH2, CH and quaternary carbon (carbon with no protons).

b) DEPT-135: The spectrum exhibits CH3 groups and CH groups as positive signals (pointing up); CH2 groups appear as negative signals (pointing down) and quaternary carbon does not appear.

The signals appear in each type of spectrum:

Organic Chemistry, Chapter 13.12, Problem 20P

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Chapter 13 Solutions

Organic Chemistry

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