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you have an unknown compound and are told that it is ONE e, CH,C2CH-CH2 f. CH,CH

ID: 552788 • Letter: Y

Question

you have an unknown compound and are told that it is ONE e, CH,C2CH-CH2 f. CH,CH CH2OH FH spectrum) (H spectrum) ('H spectrum) For the problems below: The best set of chemical shift charts and tables for help in solving these problems and those that will be given during lab are the ones in Vollhardt, p 421 for "C and p 397 for 'H and the ones in this document in the appendicies. 4. You have an unknown compound and are told that it is ONE of the two possibilities, compound A or compound B, shown below. Concisely describe how you could decide which one it is from the indicated NMR spectrum. Be specific about the significant spectral features that would be present or absent if it is A and if it is B, upon which the decision would be based. Other spectral features need not be described. H NMR Spectrum 13 C NMR Spectrum 13

Explanation / Answer

Diethyl ether (A) and isopropyl methyl ether (B):

These two can be differentiated based on number of signals in 13C NMR. A will have 2 signals while B three signals.

Tetramethylbenzene (A) and para dimethyl benzene (B):

These two can be differiated by signal intensity of methyl and aromatic protons in proton NMR. A will have aliphatic vs aromatic signal intensity ratio 6:1 while B will have 3:2