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Chapter 13: Q13-19P (page 413)

Classify the resonances in the13C NMR spectrum of methyl propanoate,CH3CH2CO2CH3.

Short Answer

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NMR Spectra

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01

13C NMR spectroscopy

Most 13C resonances are between 0 and 220 ppm downfield from the TMS reference line, with the exact chemical shift of each 13C resonance dependent on that carbon鈥檚 electronic environment within the molecule.

Generally, the chemical shift is affected by the electronegativity of a nearby atom like oxygen, nitrogen, halogen, etc.

02

13C NMR spectrum for methyl propanoate

The chemical shift value for the carbonyl carbon of ester is 174.9 ppm. While the -CH3group which is attached to the oxygen has a chemical shift value of 51.5 ppm. Also, the -CH3group which is attached to -CH2group is about 9.2 ppm. The -CH2group which is connected to carbonyl carbon has a chemical shift value of 27.5 ppm.

NMR Spectra

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Most popular questions from this chapter

A 13C NMR spectrum of commercially available 2,4-pentanediol, shows five peaks at 23.3, 23.9, 46.5, 64.8, and 68.1 d. Explain.

We saw in Section 9-3 that addition of H-Br to a terminal alkyne leads to the Markovnikov addition product, with the Br bonding to the more highly substituted carbon. How could you use 13C NMR to identify the product of theaddition of 1 equivalent of H-Br to 1-hexyne?

Compound F, a hydrocarbon with M+= 96 in its mass spectrum, undergoes reaction with HBr to yield compound G. Propose structures for F and G, 13Cwhose NMR spectral data are given below.

a. Compound F Broadband-decoupled 13CNMR: 27.6, 29.3, 32.2, 132.4 d DEPT-90: 132.4 d DEPT-135: positive peak at 132.4 d; negative peaks at 27.6, 29.3, 32.2 d

b. Compound G Broadband-decoupled 13C NMR: 25.1, 27.7, 39.9, 56.0 d DEPT-90: 56.0 d DEPT-135: positive peak at 56.0 d; negative peaks at 25.1, 27.7, 39.9 d

Question: How many electronically non-equivalent kinds of protons and how

many kinds of carbons are present in the following compound? Don鈥檛

forget that cyclohexane rings can ring-flip.

The compound whose 1H NMR spectrum is shown has the molecular

formula C3H6Br2. Propose a structure.
See all solutions

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