Purchase Solution

H NMR and C NMR

Not what you're looking for?

Ask Custom Question

In this problem the tertiary alcohol below was subjected to dehydration with phosphorous oxychloride. The potential products are shown below. The product was isolated and purified by distillation. An NMR of the major product exhibited two triplets only, one centered at 2.1δ and the other at 0.9δ . Indicate the product that seems to have been produced. Explain the spectrum.

See attached files for full problem description.

Attachments
Purchase this Solution
Solution Summary

The solution explains the spectrum and the resultant products of a dehydration of alcohol.

Solution Preview

Response to Question 8:

In compound one, we have many different kinds of hydrogen atoms. Why is that? Practically every carbon that hydrogens are attached to are different because of the position of the -OH group. That one functional group makes the entire molecule totally unsymmetrical. As a result of this asymmetry, we would expect to see all kinds of peaks for all the different hydrogens.

In compound 2, again we do not have any symmetry. Not only that but we would clearly see that the lone hydrogen off the C=C would be expected to have a chemical shift different from all the rest of hydrogens attached to the sp3 hybridized carbons, right? Also, the two hydrogens on the CH2 group that is nearest that double bond (on the pentene ring) would be split into a complex pattern because they would be split by the single hydrogen on the double bond (into a doublet) and then split again by the two hydrogens on the nearest CH2 group into a triplet, giving rise to a complicated splitting pattern. Again, because of that double bond, the carbons ...

Purchase this Solution
Free BrainMass Quizzes
Thermochemistry

The quiz helps in revising basic concepts about thermochemistry.

Periodic table

Functional groups in Organic Chemistry

You will be tested on the names of functional groups in Organic Chemistry. It is very important to know the functional groups to understand Organic reactions.

Organic Chemistry Naming: Alkanes

This is a quiz which is designed to assist students with learning the nomenclature used to identify organic compounds. This quiz focuses on the organic compounds called Alkanes.

Match Elements with their Symbols

Elements are provided: choose the matching one- or two-letter symbol for each element.

View More Free Quizzes
Related BrainMass Solutions

  • H NMR and C NMR spectra

    It finds the structures of the compounds given their H NMR and C NMR spectra. The solution has a '5/5' rating.

  • Spectroscopy Questions

    165067 NMR and IR Spectrosocopy 1) Give the Frequency ranges (in cm-1) for each of the following: a. O-H stretch b. aldehyde c. -C-H stretch d.

  • H NMR to obtain the conformation of two cyclic organic molecules

    110559 H NMR to obtain the conformation of two cyclic organic molecules NOTE: Could you please use carbohydrates as the examples of the cyclic organic molecules?

  • Interpret the H nmr spectra of 1-naphthol

    477365 Interpret the H nmr spectra of 1-naphthol Please see the attachment. Please interpret the H nmr spectra of 1-naphthol.

  • Calculation of percentage yield of nitrone

    Integration values of 1H-NMR in chloroform and ESR. 1H-NMR ESR 1.00, 0.43, 1.46, 0.61, 9.16, 4.53, 5.56, 7.43, 14.56, 4.69 Peak assignments: 1.60 (9H, tBu-H), 7.25 (m, 3H, Ph-H), 7.60 (1H, C-H), 8. 25 (2H, Ph-H).

  • NMR Spectrum and 13C Label

    The (1)H- [(13)C]-NMR method yielded high-quality (1)H-[(13)C]-NMR spectra. As a result, the (13)C labeling of [4-(13)C]-glutamate (Glu) and [4-(13)C]-glutamine (Gln) could be detected.

  • MS, IR, & NMR spectrum of an unknown compound

    The structure of a compound is elucidated using MS, Ir and NMR. All work and reasoning is included.

  • Sketching the NMR Spectrum

    The peak would be around 1 ppm as these proton nuclei wouldn't be shifted too far. 1,1,2-tribromoethane is: Br H | | H-C-C-Br | | H Br We have a total of 3 H. Two of them are equivalent (CH2) and one is different (CH).

  • NMR spectra of 3,3,5-trimethyl-cyclohexanol

    - and trans-3,3,5-trimethyl- cyclohexanol formed in this reaction, from the area under these C-H peaks.

  • Spectroscopic method to distinguish between isomeric acids

    You can run proton NMR and find appropriate H integration ratios a) 3:2:2:2:1 b)6:1:2:1 c)9:1 You can run C13 NMR and find the different ordered carbon atoms, a) 1 primary, 3 secondary b) 2 primary, 1 tertiary, 1 secondary c) 3 primary,

View More Related Solutions