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) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCOCH}_{2} \mathrm{CH}_{2} \mathrm{OCOCH}_{2} \mathrm{CH}_{3}\)

The \(^{1}H-NMR\) predictions for the molecules will have the following features: (i) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) has 3 different kinds of protons with specific splitting patterns.(ii) \(\mathrm{CH}_{3} \mathrm{CHBrCH}_{3}\) has 2 different kinds of protons and specific splitting patterns.(iii) \(\mathrm{CH}_{3} \mathrm{CHBrCHO}\) has 2 different kinds of protons and specific splitting patterns.(iv) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCOCH}_{2} \mathrm{CH}_{2} \mathrm{COOCH}_{2} \mathrm{CH}_{3}$ has 3 different kinds of protons and specific splitting patterns.(v) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCOCH}_{2} \mathrm{CH}_{2} \mathrm{OCOCH}_{2} \mathrm{CH}_{3}$ has 2 different kinds of protons and specific splitting patterns.