Repeat Problem 13-25, sketching the off-resonance-decoupled13Cspectra of the compounds.

Short Answer

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The off-resonance-decoupled carbon-NMR spectrums have been drawn for the given compounds.

Step by step solution

01

Step-1. Explanation of part (a):

In an off-resonance decoupled carbon-NMR spectrum, the coupling between each carbon atom and each hydrogen atom attached directly to it is observed.When off-resonance decoupling is used, the apparent magnitude of the coupling constants is reduced and overlap of the resulting multiplets is less frequent problem. The off-resonance decoupled spectrum retains the couplings between the carbon atom and directly attached protons but removes the couplings between the carbon and more remote protons.

Off-resonance decoupled carbon-NMR spectrum of part (a) molecule have been drawn with chemical shifts values indicated in the spectrum along with carbons which are responsible for peaks have also been assigned.

02

Step-2. Explanation of part (b):

In an off-resonance decoupled carbon-NMR spectrum, the coupling between each carbon atom and each hydrogen atom attached directly to it is observed. When off-resonance decoupling is used, the apparent magnitude of the coupling constants is reduced and overlap of the resulting multiplets is less frequent problem. The off-resonance decoupled spectrum retains the couplings between the carbon atom and directly attached protons but removes the couplings between the carbon and more remote protons.

Off-resonance decoupled carbon-NMR spectrum of part (b) molecule have been drawn with chemical shifts values indicated in the spectrum along with carbons which are responsible for peaks have also been assigned.

03

Step-3. Explanation of part (c):

In an off-resonance decoupled carbon-NMR spectrum, the coupling between each carbon atom and each hydrogen atom attached directly to it is observed. When off-resonance decoupling is used, the apparent magnitude of the coupling constants is reduced and overlap of the resulting multiplets is less frequent problem. The off-resonance decoupled spectrum retains the couplings between the carbon atom and directly attached protons but removes the couplings between the carbon and more remote protons.

Off-resonance decoupled carbon-NMR spectrum of part (c) molecule have been drawn with chemical shifts values indicated in the spectrum along with carbons which are responsible for peaks have also been assigned.

04

Step-4. Explanation of part (d):

In an off-resonance decoupled carbon-NMR spectrum, the coupling between each carbon atom and each hydrogen atom attached directly to it is observed. When off-resonance decoupling is used, the apparent magnitude of the coupling constants is reduced and overlap of the resulting multiplets is less frequent problem. The off-resonance decoupled spectrum retains the couplings between the carbon atom and directly attached protons but removes the couplings between the carbon and more remote protons.

Off-resonance decoupled carbon-NMR spectrum of part (d) molecule have been drawn with chemical shifts values indicated in the spectrum along with carbons which are responsible for peaks have also been assigned.

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Most popular questions from this chapter

A laboratory student was converting cyclohexanol to cyclohexyl bromide by using one equivalent of sodium bromide in a large excess of concentrated sulfuric acid. The major product she recovered was not cyclohexyl bromide, but a compound of formula C6H10that gave the following 13CNMR spectrum:

  1. Propose a structure for this product.
  2. Assign the peaks in the 13CNMR spectrum to the carbon atoms in the structure.
  3. Suggest modifications in the reaction to obtain a better yield of cyclohexyl bromide.

If the imaginary replacement of either of two protons forms enantiomers, then those protons are said to be enantiotopic.The NMR is not a chiral probe, and it cannot distinguish between enantiotopic protons. They are seen to be “equivalent by NMR”.

  1. Use the imaginary replacement technique to show that the two allylic protons (those on) of allyl bromide are enantiotopic.
  2. Similarly, show that the two HCprotons in cyclobutanol are enantiotopic.
  3. What other protons in cyclobutanol are enantiotopic?
  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 “15 to 20 times as large” 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 usingNMR.

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

A bottle of allyl bromide was found to contain a large amount of an impurity. A careful distillation separated the impurity, which has the molecular formula C3H60. The following 13CNMR spectrum of the impurity was obtained:

  1. Propose a structure for this impurity.
  2. Assign the peaks in the13CNMR spectrum to the carbon atoms in the structure.
  3. Suggest how this impurity arose in the allyl bromide sample.
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