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Predict the approximate chemical shifts of the protons in the following compounds.

a)Benzene

b)Cyclohexane

c)

d)

e)

f)

g)

h)

i)

j)

k)

l)

Short Answer

Expert verified

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppmof TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (a) molecule keeping in mind the factors affecting chemical shift.

Please mention that aromatic protons have chemical shift value around 7.1


The chemical shift values of protons


Step by step solution

01

Explanation of part (a):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppmof TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (a) molecule keeping in mind the factors affecting chemical shift.

Please mention that aromatic protons have chemical shift value around 7.1


The chemical shift values of protons

02

 Explanation of part (b):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (b) molecule keeping in mind the factors affecting chemical shift.

The chemical shift values of protons

03

Explanation of part (c):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift. The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (c) molecule keeping in mind the factors affecting chemical shift.

The chemical shift values of protons

04

 Step 4: Explanation of part (d):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (d) molecule keeping in mind the factors affecting chemical shift.

The chemical shift values of protons

05

Explanation of part (e):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (e) molecule keeping in mind the factors affecting chemical shift.

The chemical shift values of protons

06

Explanation of part (f):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (f) molecule keeping in mind the factors affecting chemical shift.

The chemical shift values of protons

07

Explanation of part (g):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow, as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decrease the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. The electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (g) molecule keeping in mind the factors affecting chemical shift.

Chemical shift values of protons

08

 Explanation of part (h):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (h) molecule keeping in mind the factors affecting chemical shift.

Chemical shift values of protons

09

 Explanation of part (i):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (i) molecule keeping in mind the factors affecting chemical shift.

Chemical shift values of protons

10

 Explanation of part (j):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (j) molecule keeping in mind the factors affecting chemical shift.

Chemical shift values of protons

11

Explanation of part (k):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decreases the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. Electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (k) molecule keeping in mind the factors affecting chemical shift.

The chemical shift values of protons

12

Explanation of part (l):

The NMR spectra is displayed as a plot of the applied radio frequency versus the absorption. The position on the plot at which the nuclei absorb is called the chemical shift.The range at which most NMR absorptions occur is narrow, as almost all absorptions occur downfield within 10 ppm of TMS. Electron-withdrawing groups decrease the electron density at the nucleus, deshielding the nucleus and result in larger chemical shift. The electronegativity of the atom also increases the chemical shift of attached proton.

The chemical shift values have been assigned in part (l) molecule keeping in mind the factors affecting chemical shift.

The chemical shift values of protons

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Most popular questions from this chapter

Sets of spectra are given for two compounds. For each set,

(1) Look at each spectrum individually and list the structural characteristics you can determine from that spectrum.

(2) Look ar the set of spectraas a group and purpose a tentative structure.

(3) Verify that your proposed structure accounts for the major features of each spectrum. The solution for compound 1 is given after the problem but go as far as you can before looking at the solution.

  1. Show which carbon atoms correspond with which peaks in the 13CNMR spectrum of butan-2-one (Figure 13-45).
  2. Draw the proton NMR spectrum you would expect for butan-2-one. How well do the proton chemical shifts predict the carbon chemical shifts using the โ€œ15 to 20 times as largeโ€ rule of thumbs?

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 using 13C NMR

(a)Describe how carbon NMR distinguishes these three isomers.
(b)Explain why they are difficult to distinguish using proton NMR.

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 proton NMR spectrum is of a compound of molecular formula C3H80.

  1. Propose a structure for this compound.
  2. Assign peaks to show which protons give rise to which signals in the spectrum.
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