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Chapter 13: Q2P (page 656)

Predict the chemical shifts of the protons in the following compounds

Short Answer

Expert verified

Alkene hydrogens give nearly 5.5 ppm NMR chemical shift. And the sp3hybridised carbon hydrogen give 0.8 ppm in NMR spectra.







Step by step solution

01

Alkene and sp3hydrogens

Alkene hydrogens give nearly 5.5 ppm NMR chemical shift. And the sp3hybridised carbon hydrogen give 0.8 ppm in NMR spectra.

02

 Phenyl and methyl hydrogens

Phenyl hydrogens give 7 ppm NMR chemical shift. And the methyl hybridised carbon hydrogen give 2.5 ppm in NMR spectra.

03

 Phenyl and methoxy hydrogens

Phenyl hydrogens give 7 ppm NMR chemical shift. And the methoxy hydrogen give 3.8 ppm in NMR spectra.

04

Alkene and Alkyne hydrogens

Alkene hydrogens give 5.5 ppm NMR chemical shift. And the alkyne carbon hydrogen give 2 ppm in NMR spectra.

05

Phenyl, carboxylic acid and methyl hydrogens

Phenyl hydrogens give 7 ppm NMR chemical shift. And the carboxylic acid carbon hydrogen give 13 ppm in NMR spectra and methyl is 2.5 ppm.

06

Methyl hydrogens

Methyl hydrogens give 1.8 ppm NMR chemical shift. But in presence of bromine the value is deshielded and increases near to 3.7 ppm in NMR spectra.

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Most popular questions from this chapter

A compound was isolated as a minor constituent in an extract from garden cress. Its spectra are shown here.

  1. Look at each spectrum individually and list the structural characteristics you can determine from that spectrum.
  2. Look at the set of spectra as a group and propose a tentative structure.
  3. Verify that your proposed structure accounts for the major features of each spectrum.

Question: How many signals would you expect to see in the 13CNMR of the following compounds? In each case, show which carbon atoms are equivalent in the 13CNMR.

Predict the multiplicity (the number of peaks as a result of splitting) and the chemical shift for all the protons in the following compounds.

Question:In a 300-MHz spectrometer, the protons in bromomethane absorb at a position 660 Hz downfield from TMS.

(a) What is the chemical shift of these protons?

(b) What is the chemical shift of the bromomethane protons in a 60-MHz spectrometer?

(c) How many hertz downfield from TMS would they absorb at 60 MHz?

Propose mechanisms to show the interchange of protons between ethanol molecules under

  1. Acid catalysis
  2. Base catalysis.
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