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Explain. The aim of this article to explain the application of DEPT in solving NMR spectra. Does this pattern indicate ortho, meta, or para substitution? Let’s how do we get this information in DEPT? Therefore, the compound has a double bond or a ring. Assume that diastereotopic groups are non-equivalent. a quartet counts as only one signal). P5.3: Calculate the chemical shift value (expressed in Hz, to one decimal place) of each sub-peak on the 1H-NMR doublet signal below. P5.12: Use the NMR data given to deduce structures. As an example, lets see this (stimulated) 13 C NMR combined with the DEPT experiments: Notice how the ppm values are retained but depending on the signals in DEPT we can tell if the carbon is a C, CH, CH 2 or a CH 3 group. a) Will the products 2A and 2B have identical or different 1H-NMR spectra? For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. 13C-NMR data is given for the molecules shown below. 13C-NMR data is given for the molecules shown below. Specifically, what percent of the molecules in the bottle are 2-bromopropane? P5.14: You obtain the following data for an unknown sample. However, DEPT makes things easier without the need for a lot of complicated analysis. b) a spectrum obtained on a 100 MHz instrument. Deduce its structure. However, you suspect that the bottle might be contaminated with 2-bromopropane. P5.9: Match the 1H-NMR spectra 19-24 below to their corresponding structures S-X. P5.6 :Match spectra below to their corresponding structures A-F. P5.7: Match spectra 7-12 below to their corresponding structures G-L . Do this for: a) a spectrum obtained on a 300 MHz instrument. P5.10: Match the 1H-NMR spectra 25-30 below to their corresponding structures AA-FF. P5.15:You take a 1H-NMR spectrum of a sample that comes from a bottle of 1-bromopropane. So, instead of simply saying hey this is a carbon, and this is another one, it tells us if it is a C, CH, CH2, or a CH3. The chemical shift is recorded as 1.7562 ppm, and the coupling … The isomeric pairs previously cited as giving very similar proton nmr spectra are now seen to be distinguished by carbon nmr. Notify me of followup comments via e-mail. C5.1: All of the 13C-NMR spectra shown in this chapter include a signal due to CDCl3, the solvent used in each case. But only the last structure matches the data from the DEPT experiments which indicate the presence of three CH2 groups (three negative signals in DEPT-135): I do want to mention that the structure of a double bond can be analyzed using the J coupling values and a powerful NMR spectrometer will give a resolution good enough to exclude the other candidates base on the coupling. What is the chemical shift, expressed to the nearest 0.1 Hz, of the furthest downfield sub-peak in the quartet? c) With purified 2A/2B, the researchers carried out the subsequent reaction shown below to make 3A and 3B, known as 'Mosher's esters'. And the other CH2 must be connected to the double bond since the signal is still more downfield than if it was a regular alkyl group. P5.11: Match the 1H-NMR spectra 31-36 below to their corresponding structures GG-LL. I’ll put this table for 1H NMR shifts for a reference: So, let’s put down the groups we have so far: Two of these X groups must be hydrogens because of the integration of the signal at ~4.7 ppm. P5.3: Calculate the chemical shift value (expressed in Hz, to one decimal place) of each sub-peak on the 1 H-NMR doublet signal below. P5.2: For each of the 20 common amino acids, predict the number of signals in the proton-decoupled 13 C-NMR spectrum. Complete the peak assignment column of each NMR data table. What is the chemical shift, expressed to the nearest 0.1 Hz, of the furthest downfield sub-peak in the quartet? Have questions or comments? The result of this simple equation gives the number of peaks in the signal. This is where a technique called DPET (distortionless enhancement by polarization transfer) becomes very useful. c) With purified 2A/2B, the researchers carried out the subsequent reaction shown below to make 3A and 3B, known as 'Mosher's esters'. They treated 4'-acylpyridine (1) with living yeast, and isolated the alcohol product(s) (some combination of 2A and 2B). Next, look at the signal splitting in 1H NMR; two triplets indicate a -CH2-CH2– fragment which is connected to Br on one end since it is downfield (3.3 ppm). P5.2: For each of the 20 common amino acids, predict the number of signals in the proton-decoupled 13C-NMR spectrum. Watch the recordings here on Youtube! 14.11: More Examples of \(^1H\) NMR Spectra, 14.10: The Splitting of the Signals is Described by the N + 1 Rule, 14.12: Coupling Constants Identify Coupled Protons, Organic Chemistry With a Biological Emphasis. b) Suggest a 1H-NMR experiment that could be used to determine what percent of starting material (1) got turned into product (2A and 2B). For each molecule, predict the number of signals in the 1H-NMR and the 13C-NMR spectra (do not count split peaks - eg. P5.12: Use the NMR data given to deduce structures. Deduce its structure. In case you needed, here the chemical shift values for 13C NMR: Let’s discuss a specific NMR problem where the final structure is only determined using the DEPT data. Equivalent protons give one NMR signal. P5.2: For each of the 20 common amino acids, predict the number of signals in the proton-decoupled 13C-NMR spectrum. a quartet counts as only one signal). a) Will the products 2A and 2B have identical or different 1H-NMR spectra? P5.11: Match the 1H-NMR spectra 31-36 below to their corresponding structures GG-LL. And now the interesting part realted to DEPT. There are three combinations of putting two hydrogens and a methyl group on the double bond: All of these would be good candidates based on the data from the proton and carbon NMR. Purpose a plausible structure based on the data provided. The proton and carbon NMR spectra of a compound with formula C5H9Br is shown below. C5.2: Researchers wanted to investigate a reaction which can be catalyzed by the enzyme alcohol dehydrogenase in yeast. First, determine the hydrogen deficiency index.

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