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

Short Answer

Expert verified

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

Determine the number of different kinds of protons in each compounds

  1. 1-bromopropane (b) 2-bromopropane
  2. 2,2-dimethylpropane (d) 2,2-dimethylpentane
  3. (e) 1-chloro-4-methylbenzene (f) 1-chloro-2-methylbenzene

A new chemist moved into an industrial lab where work was being done on oxygenated gasoline additives. Among the additives that had been tested, she found an old bottle containing a clear, pleasant-smelling liquid that was missing its label. She took the quick NMR spectrum shown and was able to determine the identity of the compound without any additional information. Propose a structure and assign the peaks. (Hint: This is a very pure sample.)

Question: An unknown compound has the molecular formula C9H11Br. Its proton NMR spectrum shows the following absorptions: singlet, d7.1, integral 44 mm singlet, d2.3, integral 130 mm singlet, d2.2, integral 67 mm Propose a structure for this compound.

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 โ€œequivalent by NMRโ€.

  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?

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?

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