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Predict which carbon will have the most upfield signal in the ¹³C NMR spectrum.

A. Carbon in an alkane
B. Carbon in an alkene
C. Carbon in an alkyne
D. Carbon in an aromatic compound

1 Answer

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Final answer:

In 13C NMR spectroscopy, the most upfield signal for a carbon atom is typically associated with the least deshielded environment. Aromatic carbons, due to their conjugated pi-electron systems, appear upfield relative to highly electronegative environments, but more downfield than alkanes.

Step-by-step explanation:

The carbon that will have the most upfield signal in a 13C NMR spectrum is typically the one that is least deshielded, meaning it experiences the least electron-withdrawing effects from its neighbors. In aromatic compounds, the carbon atoms are part of a system of conjugated pi electrons, which tend to shield the carbon nuclei to some extent.

In the aromatic compound, the carbons are more deshielded than alkane carbons due to the electron-withdrawing effect of the pi-electron cloud, but they are typically more shielded than carbons in carbonyl groups, alcohols, or carbons bonded to electronegative atoms like oxygen or nitrogen. As a result, carbons in aromatic compounds generally appear upfield compared to these more deshielded environments.

Useful reference points and additional information can be obtained by analyzing different functional groups' absorption peaks, such as those from carbonyl groups at about 1716 cm¹ or the broad peak around 3400 cm¹ for alcohol O-H stretching. The specific chemical shift for an aromatic carbon in a 13C NMR spectrum can vary, but generally, it will be more upfield compared to signals from carbons in highly electronegative environments.

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