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Three 13C and 1H NMR Questions

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For the compound below, determine how many peaks would be present in the compound's normal 13C decoupled spectrum.

Propose structures for compounds that fit the following data: C3H6Br2; 2H quintet at 2.4 ppm J = 6 Hz; 4H triplet at 3.5 ppm J = 6 Hz

Draw structures for 2-methyl-1,3-butadiene

For the compound below, determine how many peaks would be present in the compound's normal 13C decoupled spectrum.

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The solution shows the answers to problems relating proton and carbon NMR.

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General Organic Chemistry Questions

(a) How many resonance structures are there for the cyclohepatrienyl cation? Draw them.

(b) Are carbon-carbon bonds equivalent?

(c) How many peaks would you expect to see in the 1H NMR as well as the 13C NMR spectra of this cation?

(d) Use the Frost Circle to draw the energy levels of the Pi molecular orbitals for this ion, show the electronic configuration and explain why the ion is aromatic.

(e) Does it obey the Huckel rule?

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