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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 small pilot was adding bromine across the double bond of but-2-ene to make 2,3-dibromobutane. A controller malfunction allowed the reaction temperature to rise beyond safe limits. A careful distillation of the product showed that several impurities had formed, including the one having the NMR spectra that appear below. Determine its structure and assign the peaks to the protons in your structure.

The three isomers of dichlorobenzene are commonly named ortho-chlorobenzene, meta-chlorobenzene, and para-chlorobenzene. These three isomers are difficult to distinguish using proton NMR, but they are instantly identifiable usingNMR.

  1. Describe how carbon NMR distinguishes these three isomers.
  2. Explain why they are difficult to distinguish using proton NMR.

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

  1. Acid catalysis
  2. Base catalysis.

For each compound shown below,

  1. Sketch theC13NMR spectrum (totally decoupled, with a singlet for each type of carbon), showing approximate chemical shifts.
  2. Show the multiplicity expected for each signal in the off-resonance-decoupled spectrum.
  3. Sketch the spectra expected using the DEPT-90 and DEPT-135 techniques.

The following spectra are taken from a compound that is an important starting material for organic synthesis. Determine the structure, first by considering each spectrum individually, and then by considering all the spectra together. Assign peaks to show that your proposed structure accounts for all the major features of each spectrum. DEPT information is given in blue on the carbon NMR
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