Question 4 (13 pts). Summarize the NMR data for the carvone addition product. So

Question

Question 4 (13 pts). Summarize the NMR data for the carvone addition product. Some cells may be inapplicable to the structure in which case write N/A. Other cells may need to be split into multiple rows as in the previous table. CI Chemical ShiftIntegration Discernable Splitting Pattern* most deshielded vinyl hydrogen(s) less deshielded vinyl hydrogen(s) ring sp hydrogen(s) methyl hydrogens *If a signal corresponds to a single, unique type of hydrogen but is not a singlet, then report the chemical shift as being the center of the peaks. If the signals for different, unique hydrogens are overlapping, then report the chemical shift as a range. **If a signal has an identifiable, regular shape such as singlet, doublet, triplet, doublet of doublets, then report that splitting pattern. If the signal is complicated, irregular, and unidentifiable, then multiplet is the proper way to report it. *Total integration for region

Explanation / Answer

For the given structure shown above

The 1H NMR prediction would be,

1.5 ppm (singlet, 6H) for two CH3's next to quaternary C-Cl

1.7 ppm (singlet, 3H) for CH3 on alkenic carbon

2.4 ppm (doublet, 2H) for CH2 between CH and C=O

1.9 ppm (quartet, 1H) for CH between CH2 and CH

2.2 ppm (doublet or doublet, 2H) for CH2 between aliphatic CH and alkenic CH

5.5 ppm (doublet, 1H) for alkenic hydrogen

IR spectrum

2974 cm-1 for sp3 -C-H stretch

1675 cm-1 for C=O stretch

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