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Question 11.1: Predicting Chemical Shifts in 13C NMR Spectra At what approx...

Predicting Chemical Shifts in ^{13}C NMR Spectra

At what approximate positions would you expect ethyl acrylate, H_{2}C=CHCO_{2}CH_{2}CH_{3}, to show^{13}C NMR absorptions?

Strategy
Identify the distinct carbons in the molecule, and note whether each is alkyl, vinylic, aromatic, or in a carbonyl group. Then predict where each absorbs, using Figure 11.7 as necessary.

 

11.7
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Ethyl acrylate has five distinct carbons: two different C=C, one C=O, one O–C, and one alkyl C. From Figure 11.7, the likely absorptions are

 

The actual absorptions are at 14.1, 60.5, 128.5, 130.3, and 166.0 \delta .

11.7

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