Chapter 13: Q19P (page 677)
Propose mechanisms to show the interchange of protons between ethanol molecules under
- Acid catalysis
- Base catalysis.
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Chapter 13: Q19P (page 677)
Propose mechanisms to show the interchange of protons between ethanol molecules under
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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:

The following spectra are taken from a compound that is an important starting material for organic synthesis. Determine the structure, first by considering each spectrum individually, and then by considering all the spectra together. Assign peaks to show that your proposed structure accounts for all the major features of each spectrum. DEPT information is given in blue on the carbon NMR


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.

Predict the theoretical number of different NMR signals produced by each compound and give approximate chemical shifts. Point out any diastereotopic relationships.
Predict the chemical shifts of the protons in the following compounds
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