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Sets of spectra are given for two compounds. For each set, (1) look at each spectrum

Chapter 13, Problem PROBLEM 13-32

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QUESTION:

Sets of spectra are given for two compounds. For each set, (1) look at each spectrum individually, and list the structural characteristics you can determine from that spectrum. (2) look at the set of spectra as a group, and propose a tentative structure. (3) verify that your proposed structure accounts for the major features of each spectrum. The solution for compound 1 is given after the problem, but go as far as you can before looking at the solution.

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QUESTION:

Sets of spectra are given for two compounds. For each set, (1) look at each spectrum individually, and list the structural characteristics you can determine from that spectrum. (2) look at the set of spectra as a group, and propose a tentative structure. (3) verify that your proposed structure accounts for the major features of each spectrum. The solution for compound 1 is given after the problem, but go as far as you can before looking at the solution.

ANSWER:

Step 1 of 6

For compound :

The given mass spectrum is concluded that the large even-numbered fragment at  and odd-number molecular weight at . Thus, the presence of nitrogen atom  is confirmed.

The given infrared spectrum is illustrated that a sharp peak observes at . Thus, it confirms the presence of  bond of an amine group or  of terminal alkyne. The peak of unsaturated  observes above . The peak of the  stretch of the aromatic ring shows at .

The given NMR spectrum represents that the compound split in the aromatic region. The five integral confirms the monosubstituted ring.  The absorption at  depicts that the pi-electron group is present as a substituent on a benzene ring.  The peak at  and   confirms the presence of the ethyl group.

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