Question: Sketch what you might expect the1H and13C NMR spectra of the following compound to look like (green=Cl):

Short Answer

Expert verified

The compound has 5 different type of carbons and 4 different type of hydrogen.

Step by step solution

01

NMR spectroscopy

NMR stands for Nuclear Magnetic Resonance Spectroscopy. This is the technique used for determining the structure of the organic compounds. It is a non-destructive technique. It is of two types1H NMR and13C NMR.

Proton nuclear magnetic resonance (1H NMR) is the application of nuclear magnetic resonance in NMR spectroscopy with respect to hydrogen-1 nuclei within in the molecule of substance in order to determine the structure of its molecules.

Carbon-13 nuclear magnetic resonance is the application of nuclear magnetic resonance spectroscopy to carbon. It is analogous to proton NMR and allows the identification of carbon atom in an organic molecule just as proton NMR identifies Hydrogen atoms.

02

Number of signals and their relative intensities

The number of signals present in NMR reflects the number of magnetically different protons. Thus the number of signal reflects the number of chemically different protons or sets of protons. For example methanol has two different set of protons (methyl and hydroxyl).

The relative intensities of the signal reflects the relative number of protons of different kind present in the molecule, for example

CH3CH2OH: Three types of protons, three NMR signals.

So, relative intensities: 3:2:1

03

Sketch the 1H and 13C NMR spectra of the following compound

The compound has 5 different type of carbons and 4 different type of hydrogen.

No. of signal = 5 No. of signal = 4





1H and 13C NMR spectra of the ethyl-2-chloropropanoate

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Compound A, a hydrocarbon with M+= 96 in its mass spectrum, has theC13 spectral data given below. On reaction withBH3 , followed by treatment with basic H2O2, A is converted into B, whoseC13 spectral data are also given below. Propose structures for A and B.

Compound A Broadband-decoupledC13 NMR: 26.8, 28.7, 35.7, 106.9, 149.7 d DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 d

Compound B Broadband-decoupledC13 NMR: 26.1, 26.9, 29.9, 40.5, 68.2 d DEPT-90: 40.5 d DEPT-135: positive peak at 40.5 d; negative peaks at 26.1, 26.9, 29.9, 68.2 d

Propose a structure for compound C, which has M+= 86 in its mass spectrum, an IR absorption at 3400cm-1, and the following C13NMR spectral data:

Compound C Broadband-decoupled C13 NMR: 30.2, 31.9, 61.8, 114.7, 138.4 d DEPT-90: 138.4 d DEPT-135: positive peak at 138.4 d; negative peaks at 30.2, 31.9, 61.8, 114.7 d

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?

The amount of energy required to spin-flip a nucleus depends both on the strength of the external magnetic field and on the nucleus. At a field strengthof 4.7 T, rf energy of 200 MHz is required to bring a H1nucleus into resonance, but energy of only 187 MHz will bring a F19nucleus into resonance. Calculate the amount of energy required to spin-flip a F19nucleus. Is this amount greateror less than that required to spin-flip a H1nucleus?

How many 13C NMR absorptions would you expect for cis-1,3-dimethylcyclohexane?For trans-1,3-dimethylcyclohexane? Explain.

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free