Chapter 37

Predict the \({ }^{1}\) H-NMR spectra of the following molecules. Note: only the number of different hydrogen atoms needs to be stated and coupling patterns must be deduced. (i) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) (ii) \(\mathrm{CH}_{3} \mathrm{CHBrCH}_{3}\) (iii) \(\mathrm{CH}_{3} \mathrm{CHBrCHO}\) (iv) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCOCH}_{2} \mathrm{CH}_{2} \mathrm{COOCH}_{2} \mathrm{CH}_{3}\) (v) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCOCH}_{2} \mathrm{CH}_{2} \mathrm{OCOCH}_{2} \mathrm{CH}_{3}\)

Predict the \({ }^{13}\) C-NMR spectra of the following molecules. Note: only the number of different carbon atoms needs to be given and the \({ }^{13} \mathrm{C}-{ }^{1} \mathrm{H}\) coupling patterns deduced. (i) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}\) (ii) \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{OCH}_{3}\) (iii) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{COOCH}_{2} \mathrm{CH}_{3}\right)_{2}\) (iv) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\) (v) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{3}\)